Aufsatz
Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese
Prof. Dr. Thorsten Bach,
Dipl.-Chem. Jörg P. Hehn,
Corresponding Author
Prof. Dr. Thorsten Bach
Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstraße 4, 85747 Garching (Deutschland), Fax: (+49) 89-289-13315 http://www.oc1.ch.tum.de/
Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstraße 4, 85747 Garching (Deutschland), Fax: (+49) 89-289-13315 http://www.oc1.ch.tum.de/Search for more papers by this authorDipl.-Chem. Jörg P. Hehn
Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstraße 4, 85747 Garching (Deutschland), Fax: (+49) 89-289-13315 http://www.oc1.ch.tum.de/
Search for more papers by this authorProf. Dr. Thorsten Bach,
Dipl.-Chem. Jörg P. Hehn,
Corresponding Author
Prof. Dr. Thorsten Bach
Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstraße 4, 85747 Garching (Deutschland), Fax: (+49) 89-289-13315 http://www.oc1.ch.tum.de/
Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstraße 4, 85747 Garching (Deutschland), Fax: (+49) 89-289-13315 http://www.oc1.ch.tum.de/Search for more papers by this authorDipl.-Chem. Jörg P. Hehn
Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstraße 4, 85747 Garching (Deutschland), Fax: (+49) 89-289-13315 http://www.oc1.ch.tum.de/
Search for more papers by this authorAbstract
Photochemische Reaktionen bereichern in signifikanter Weise das Repertoire zur Knüpfung von Kohlenstoff-Kohlenstoff-Bindungen und machen ungewöhnliche, auf herkömmlichem Weg nicht erhältliche Molekülgerüste zugänglich. In diesem Aufsatz werden die wichtigsten Umsetzungen der Photochemie vorgestellt, die auf breiter Front Einzug in die Naturstoffsynthese gehalten haben. Beispielhaft werden einzelne Totalsynthesen diskutiert, wobei besonderes Augenmerk auf den photochemischen Schlüsselschritt sowie dessen Stereoselektivität gerichtet ist. Dabei wird das photochemisch erzeugte Molekül in Relation zur Struktur des Naturstoffs gebracht, und Folgereaktionen werden, wo notwendig, illustriert und klassifiziert.
References
- 1Bestandsaufnahmen zum Stand der organischen Synthese:
- 1aD. Seebach, Angew. Chem. 1990, 102, 1363–1409; Angew. Chem. Int. Ed. Engl. 1990, 29, 1320–1367;
- 1bK. C. Nicolaou, D. Vourloumis, N. Winssinger, P. S. Baran, Angew. Chem. 2000, 112, 46–126;
10.1002/(SICI)1521-3757(20000103)112:1<46::AID-ANGE46>3.0.CO;2-P Google ScholarAngew. Chem. Int. Ed. 2000, 39, 44–122.10.1002/(SICI)1521-3773(20000103)39:1<44::AID-ANIE44>3.0.CO;2-L CAS PubMed Web of Science® Google Scholar
- 2
- 2aR. B. Woodward in Perspectives in Organic Chemistry (Hrsg.: ), Interscience, New York, 1956, S. 155–184;
- 2bN. Anand, J. S. Bindra, S. Ranganathan, Art in Organic Synthesis, Holden-Day, San Francisco, 1970.
- 3
- 3aJ. B. Hendrickson, J. Am. Chem. Soc. 1975, 97, 5784–5800;
- 3bB. Trost, Science 1991, 254, 1471–1477;
- 3cP. A. Wender, M. P. Croatt, B. Witulski, Tetrahedron 2006, 62, 7505–7511;
- 3dP. A. Wender, V. A. Verma, T. J. Paxton, T. H. Pillow, Acc. Chem. Res. 2008, 41, 40–49;
- 3eN. Z. Burns, P. S. Baran, R. W. Hoffmann, Angew. Chem. 2009, 121, 2896–2910;
10.1002/ange.200806086 Google ScholarAngew. Chem. Int. Ed. 2009, 48, 2854–2867.
- 4E. J. Corey, X.-M. Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1989.
- 5Aktuelle Übersichten zum Stand der organischen Photochemie:
- 5aC.-L. Ciana, C. G. Bochet, Chimia 2007, 61, 650–654;
- 5bN. Hoffmann, J.-C. Gramain, H. Bouas-Laurent, Actual. Chim. 2008, 317, 6–13;
- 5cN. Hoffmann, Chem. Rev. 2008, 108, 1052–1103.
- 6Als Unterscheidung zwischen racemisch oder enantioselektiv hergestellten Naturstoffen wird, wo möglich, die Drehrichtung der spezifischen Rotation verwendet, also (±)- für racemische, (+)- oder (−)- für enantiomerenreine Produkte. Überdies findet die Konvention Verwendung, wonach die Relativkonfiguration von Racematen durch gerade Balken (fett oder gestrichelt), die Absolut- und Relativkonfiguration enantiomerenreiner Verbindungen in Keilform (fett oder gestrichelt) dargestellt wird: H. Maehr, J. Chem. Educ. 1985, 62, 114–120.
- 7P. A. Wender, J. J. Howbert, J. Am. Chem. Soc. 1981, 103, 688–690.
- 8E. Coyle, M. Oelgemöller, Photochem. Photobiol. Sci. 2008, 7, 1313–1322.
- 9Übersichten:
- 9aA. Gilbert in CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. ), CRC, Boca Raton, 2004, S. 33/1–33/11;
- 9bA. Gilbert in CRC Handbook of Organic Photochemistry and Photobiology (Hrsg.: ), CRC, Boca Raton, 1995, S. 291–300;
- 9cF. B. Mallory, C. W. Mallory, Org. React. 1984, 30, 1–456;
- 9dW. G. Dauben, E. L. McInnis, D. M. Michno in Rearrangements in Ground and Excited States (Hrsg.: ), Academic Press, New York, 1980, S. 91–123.
10.1016/B978-0-12-481303-8.50008-1 Google Scholar
- 10Übersicht: G. Mann, H. M. Muchall in Methoden Org. Chem. (Houben-Weyl), Vol. E 17f, 4th ed., 1997, S. 667–684.
- 11Übersicht: A. G. Schultz, L. Motyka, Org. Photochem. 1983, 6, 1–119.
- 12J.-C. Gramain, H. P. Husson, Y. Troin, J. Org. Chem. 1985, 50, 5517–5520.
- 13
- 13aM. Dufour, J.-C. Gramain, H.-P. Husson, M.-E. Sinibaldi, Y. Troin, Tetrahedron Lett. 1989, 30, 3429–3432;
- 13bM. Dufour, J.-C. Gramain, H.-P. Husson, M.-E. Sinibaldi, Y. Troin, J. Org. Chem. 1990, 55, 5483–5490;
- 13cM. Dufour, J.-C. Gramain, H. P. Husson, M. E. Sinibaldi, Y. Troin, Synth. Commun. 1992, 22, 189–200.
- 14H. Kinoshita, T. Ohnuma, T. Oishi, Y. Ban, Chem. Lett. 1986, 15, 927–930.
- 15A. G. Schultz, Y. K. Yee, M. H. Berger, J. Am. Chem. Soc. 1978, 100, 8065–8067.
- 16
- 16aP. Sharma, N. Griffiths, J. E. Moses, Org. Lett. 2008, 10, 4025–4027;
- 16bP. Sharma, J. E. Moses, Synlett 2010, 525–528.
- 17S. J. Eade, M. W. Walter, C. Byrne, B. Odell, R. Rodriguez, J. E. Baldwin, R. M. Adlington, J. E. Moses, J. Org. Chem. 2008, 73, 4830–4839.
- 18R. G. S. Berlinck, R. Britton, E. Piers, L. Lim, M. Roberge, R. Moreira da Rocha, R. J. Andersen, J. Org. Chem. 1998, 63, 9850–9856.
- 19M. Gallant, J. T. Link, S. J. Danishefsky, J. Org. Chem. 1993, 58, 343–349.
- 20
- 20aA. Fürstner, M. M. Domostoj, B. Scheiper, J. Am. Chem. Soc. 2005, 127, 11620–11621;
- 20bA. Fürstner, M. M. Domostoj, B. Scheiper, J. Am. Chem. Soc. 2006, 128, 8087–8094.
- 21
- 21aJ. B. Hendrickson, J. G. De Vries, J. Org. Chem. 1982, 47, 1148–1150;
- 21bJ. B. Hendrickson, J. G. De Vries, J. Org. Chem. 1985, 50, 1688–1695.
- 22M. Ishikura, A. Hino, T. Yaginuma, I. Agata, N. Katagiri, Tetrahedron 2000, 56, 193–207.
- 23
- 23aB. Sarstedt, E. Winterfeldt, Heterocycles 1983, 20, 469–476;
- 23bG. Xie, J. William Lown, Tetrahedron Lett. 1994, 35, 5555–5558.
- 24J. L. Wood, B. M. Stoltz, S. N. Goodman, K. Onwueme, J. Am. Chem. Soc. 1997, 119, 9652–9661.
- 25E. M. Beccalli, F. Clerici, A. Marchesini, Tetrahedron 1998, 54, 11675–11682.
- 26E. C. Miranda, C. H. Brieskorn, S. Blechert, Chem. Ber. 1980, 113, 3245–3248.
- 27Y. Kobayashi, T. Fujimoto, T. Fukuyama, J. Am. Chem. Soc. 1999, 121, 6501–6502.
- 28S. B. Singh, G. R. Pettit, J. Org. Chem. 1989, 54, 4105–4114.
- 29D. Kaliakoudas, C. H. Eugster, P. Rüedi, Helv. Chim. Acta 1990, 73, 48–62.
- 30S. M. Kupchan, H. C. Wormser, J. Org. Chem. 1965, 30, 3792–3800.
- 31R. B. Herbert, C. J. Moody, J. Chem. Soc. Chem. Commun. 1970, 121.
- 32R. M. Letcher, K.-M. Wong, J. Chem. Soc. Perkin Trans. 1 1979, 2449–2450.
- 33F. M. Moghaddam, M. M. Farimani, Tetrahedron Lett. 2010, 51, 540–542.
- 34T. R. Kelly, C. T. Jagoe, Q. Li, J. Am. Chem. Soc. 1989, 111, 4522–4524.
- 35G. Mehta, S. R. Shah, Y. Venkateswarlu, Tetrahedron 1994, 50, 11729–11742.
- 36G. R. Lenz, Synthesis 1978, 489–518.
- 37M. P. Cava, P. Stern, K. Wakisaka, Tetrahedron 1973, 29, 2245–2249.
- 38S. M. Kupchan, J. L. Moniot, R. M. Kanojia, J. B. O’Brien, J. Org. Chem. 1971, 36, 2413–2418.
- 39
- 39aM. P. Cava, S. C. Havlicek, A. Lindert, R. J. Spangler, Tetrahedron Lett. 1966, 7, 2937–2966;
10.1016/S0040-4039(01)99891-0 Google Scholar
- 39bM. P. Cava, M. J. Mitchell, S. C. Havlicek, A. Lindert, R. J. Spangler, J. Org. Chem. 1970, 35, 175–179.
- 40M. P. Cava, S. S. Libsch, J. Org. Chem. 1974, 39, 577–578.
- 41D.-M. Zhou, B.-Z. Yue, J.-Q. Cui, M.-S. Cai, L.-H. Zhang, Heterocycles 1997, 45, 367–383.
- 42L. Cleaver, S. Nimgirawath, E. Ritchie, W. Taylor, Aust. J. Chem. 1976, 29, 2003–2021.
- 43L. Castedo, R. J. Estévez, J. M. Saá, R. Suau, J. Heterocycl. Chem. 1982, 19, 1319–1323.
- 44L. Castedo, J. M. Saá, R. Suau, J. C. Estévez, An. Quim. 1983, 79, 329–332.
- 45L. Castedo, J. A. Granja, A. R. D. Lera, M. C. Villaverde, J. Heterocycl. Chem. 1988, 25, 1561–1566.
- 46J. C. Estévez, M. C. Villaverde, R. J. Estévez, J. A. Seijas, L. Castedo, Can. J. Chem. 1990, 68, 964–968.
- 47M. C. Pampín, J. C. Estévez, L. Castedo, R. J. Estévez, Tetrahedron Lett. 2001, 42, 2307–2308.
- 48M. C. Pampín, J. C. Estévez, R. J. Estévez, R. Suau, L. Castedo, Tetrahedron 2003, 59, 8057–8065.
- 49H. Iida, C. Kibayashi, Tetrahedron Lett. 1981, 22, 1913–1914.
- 50O. Blanco, L. Castedo, M. Cid, J. A. Seijas, C. Villaverde, Heterocycles 1990, 31, 1077–1080.
- 51D. Becker, L. R. Hughes, R. A. Raphael, J. Chem. Soc. Perkin Trans. 1 1977, 1674–1681.
- 52E. Ghera, Y. Ben-David, D. Becker, Tetrahedron Lett. 1977, 18, 463–466.
10.1016/S0040-4039(01)92666-8 Google Scholar
- 53
- 53aL. Castedo, J. S. Saá, R. Suau, G. Tojo, Tetrahedron Lett. 1983, 24, 5419–5420;
- 53bI. Ben, L. Castedo, J. M. Saa, J. A. Seijas, R. Suau, G. Tojo, J. Org. Chem. 1985, 50, 2236–2240.
- 54
- 54aA. S. Kende, D. P. Curran, Tetrahedron Lett. 1978, 19, 3003–3006;
10.1016/S0040-4039(01)94923-8 Google Scholar
- 54bA. S. Kende, D. P. Curran, J. Am. Chem. Soc. 1979, 101, 1857–1864.
- 55E. McDonald, R. T. Martin, Tetrahedron Lett. 1978, 19, 4723–4726.
10.1016/S0040-4039(01)85715-4 Google Scholar
- 56M. Onda, K. Yonezawa, K. Abe, Chem. Pharm. Bull. 1971, 19, 31–36.
- 57M. D. Markey, Y. Fu, T. R. Kelly, Org. Lett. 2007, 9, 3255–3257.
- 58Y. Hayashi, T. Matsumoto, M. Nishizawa, M. Togami, T. Hyono, N. Nishikawa, M. Uemura, T. Sakan, J. Org. Chem. 1982, 47, 3428–3433.
- 59Beispiele dieser Reaktion finden sich unter anderem in der Synthese von Vitamin D und seinen Derivaten. Allgemeine Übersicht: G.-D. Zhu, W. H. Okamura, Chem. Rev. 1995, 95, 1877–1952, zit. Lit.; historischer Rückblick: G. Wolf, J. Nutr. 2004, 134, 1299–1302.
- 60Anwendung der photochemischen Ringöffnung von 1,3-Cyclohexadienen:
- 60aE. J. Corey, A. G. Hortmann, J. Am. Chem. Soc. 1963, 85, 4033–4034 [(+)-Dihydrocostunolid];
- 60bY. Fujimoto, T. Shimizu, T. Tatsuno, Tetrahedron Lett. 1976, 17, 2041–2044 [(+)-Dihydrocostunolid];
10.1016/S0040-4039(00)93812-7 Google Scholar
- 60cG. Quinkert, K. R. Schmieder, G. Dürner, K. Hache, A. Stegk, D. H. R. Barton, Chem. Ber. 1977, 110, 3582–3614 [Dimethylcrocetin].
- 61
- 61aG. Quinkert, N. Heim, J. Glenneberg, U.-M. Billhardt, V. Autze, J. W. Bats, G. Dürner, Angew. Chem. 1987, 99, 363–365; Angew. Chem. Int. Ed. Engl. 1987, 26, 362–364;
- 61bG. Quinkert, N. Heim, J. Glenneberg, U. Döller, M. Eichhorn, U.-M. Billhardt, C. Schwarz, G. Zimmermann, J. W. Bats, G. Dürner, Helv. Chim. Acta 1988, 71, 1719–1794.
- 62Übersichten:
- 62aT. Naito, Chem. Pharm. Bull. 2008, 56, 1367–1383;
- 62bI. Ninomiya, T. Kiguchi, T. Naito in The Alkaloids, Vol. 50 (Hrsg.: ), Academic Press, New York, 1998, S. 317–342;
- 62cI. Ninomiya, J. Nat. Prod. 1992, 55, 541–564;
- 62dI. Ninomiya, T. Naito, Heterocycles 1981, 15, 1433–1462.
- 63
- 63aI. Ninomiya, H. Takasugi, T. Naito, J. Chem. Soc. Chem. Commun. 1973, 732;
- 63bI. Ninomiya, T. Naito, H. Takasugi, J. Chem. Soc. Perkin Trans. 1 1976, 1865–1868.
- 64I. Ninomiya, T. Naito, Heterocycles 1974, 2, 607–609.
- 65T. Naito, O. Miyata, I. Ninomiya, S. C. Pakrashi, Heterocycles 1981, 16, 725–728.
- 66
- 66aM. Sainsbury, B. Webb, Phytochemistry 1975, 14, 2691–2693;
- 66bM. Sainsbury, N. L. Uttley, J. Chem. Soc. Perkin Trans. 1 1976, 2416–2418.
- 67T. Naito, E. Doi, O. Miyata, I. Ninomiya, Heterocycles 1986, 24, 903–906.
- 68T. Naito, E. Kuroda, O. Miyata, I. Ninomiya, Chem. Pharm. Bull. 1991, 39, 2216–2218.
- 69I. Ninomiya, T. Naito, H. Ishii, Heterocycles 1975, 3, 307–309.
- 70S. V. Kessar, G. Singh, P. Balakrishnan, Tetrahedron Lett. 1974, 15, 2269–2270.
10.1016/S0040-4039(01)92230-0 Google Scholar
- 71T. Kametani, T. Sugai, Y. Shoji, T. Honda, F. Satoh, K. Fukumoto, J. Chem. Soc. Perkin Trans. 1 1977, 1151–1155.
- 72I. Ninomiya, T. Naito, J. Chem. Soc. Chem. Commun. 1973, 137.
- 73I. Ninomiya, T. Naito, H. Takasugi, J. Chem. Soc. Perkin Trans. 1 1975, 1720–1724.
- 74T. Kametani, T. Honda, T. Sugai, K. Fukumoto, Heterocycles 1976, 4, 927–932.
- 75I. Ninomiya, H. Takasugi, T. Naito, Heterocycles 1973, 1, 17–20.
- 76I. Ninomiya, T. Naito, H. Takasugi, J. Chem. Soc. Perkin Trans. 1 1975, 1791–1795.
- 77I. Ninomiya, Y. Tada, O. Miyata, T. Naito, Heterocycles 1980, 14, 631–633.
- 78S. C. Pakrashi, R. Mukhopadhyay, P. P. G. Dastidar, A. Bhattacharjya, E. Ali, Tetrahedron Lett. 1983, 24, 291–294.
- 79
- 79aI. Ninomiya, O. Yamamoto, T. Naito, Heterocycles 1977, 7, 137–141;
- 79bI. Ninomiya, O. Yamamoto, T. Naito, J. Chem. Soc. Perkin Trans. 1 1983, 2171–2174.
- 80H. Ishii, E. Ueda, K. Nakajima, T. Ishida, T. Ishikawa, K.-I. Harada, I. Ninomiya, T. Naito, T. Kiguchi, Chem. Pharm. Bull. 1978, 26, 864–873.
- 81H. Iida, S. Aoyagi, C. Kibayashi, J. Chem. Soc. Chem. Commun. 1974, 499.
- 82
- 82aI. Ninomiya, T. Naito, T. Kiguchi, J. Chem. Soc. Chem. Commun. 1970, 1669–1670;
- 82bI. Ninomiya, T. Naito, T. Kiguchi, J. Chem. Soc. Perkin Trans. 1 1973, 2261–2264.
- 83G. R. Lenz, J. Org. Chem. 1974, 39, 2846–2851.
- 84
- 84aI. Ninomiya, O. Yamamoto, T. Naito, J. Chem. Soc. Chem. Commun. 1976, 437;
- 84bI. Ninomiya, O. Yamamoto, T. Naito, J. Chem. Soc. Perkin Trans. 1 1980, 212–216.
- 85I. Kato, M. Higashimoto, O. Tamura, H. Ishibashi, J. Org. Chem. 2003, 68, 7983–7989.
- 86I. Ninomiya, Y. Tada, T. Kiguchi, O. Yamamoto, T. Naito, Heterocycles 1978, 9, 1527–1531.
- 87M. Ibrahim-Ouali, M.-È. Sinibaldi, Y. Troin, D. Guillaume, J.-C. Gramain, Tetrahedron 1997, 53, 16083–16096.
- 88T. Kametani, N. Takagi, M. Toyota, T. Honda, K. Fukumoto, J. Chem. Soc. Perkin Trans. 1 1981, 2830–2834.
- 89
- 89aJ. H. Rigby, M. E. Mateo, J. Am. Chem. Soc. 1997, 119, 12655–12656;
- 89bJ. H. Rigby, U. S. M. Maharoof, M. E. Mateo, J. Am. Chem. Soc. 2000, 122, 6624–6628.
- 90
- 90aO. Miyata, Y. Hirata, T. Naito, I. Ninomiya, J. Chem. Soc. Chem. Commun. 1983, 1231–1232;
- 90bT. Naito, Y. Hirata, O. Miyata, I. Ninomiya, J. Chem. Soc. Perkin Trans. 1 1988, 2219–2225.
- 91L. Töke, K. Honty, C. Szántay, Chem. Ber. 1969, 102, 3248–3259.
- 92
- 92aO. Miyata, Y. Hirata, T. Naito, I. Ninomiya, Heterocycles 1984, 22, 1041–1044;
- 92bT. Naito, Y. Hirata, O. Miyata, I. Ninomiya, M. Inoue, K. Kamiichi, Chem. Pharm. Bull. 1989, 37, 901–906.
- 93T. Naito, Y. Tada, I. Ninomiya, Heterocycles 1981, 16, 1141–1143.
- 94
- 94aT. Naito, N. Kojima, O. Miyata, I. Ninomiya, J. Chem. Soc. Chem. Commun. 1985, 1611–1612;
- 94bT. Naito, N. Kojima, O. Miyata, I. Ninomiya, Chem. Pharm. Bull. 1986, 34, 3530–3533.
- 95T. Naito, Y. Habuo, O. Miyata, I. Ninomiya, H. Ohishi, Chem. Pharm. Bull. 1992, 40, 602–608.
- 96T. Naito, N. Kojima, O. Miyata, I. Ninomiya, Heterocycles 1986, 24, 2117–2120.
- 97T. Naito, O. Miyata, N. Kida, K. Namato, I. Ninomiya, Chem. Pharm. Bull. 1990, 38, 2419–2423.
- 98T. Kiguchi, Y. Yuumoto, I. Ninomiya, T. Naito, Chem. Pharm. Bull. 1997, 45, 1212–1215.
- 99T. Kiguchi, C. Hashimoto, T. Naito, I. Ninomiya, Heterocycles 1982, 19, 2279–2282.
- 100I. Ninomyia, C. Hashimoto, T. Kiguchi, T. Naito, J. Chem. Soc. Perkin Trans. 1 1985, 941–948.
- 101T. Naito, O. Miyata, I. Ninomiya, Heterocycles 1987, 26, 1739–1742.
- 102I. Ninomiya, T. Naito, O. Miyata, T. Shinada, E. Winterfeldt, R. Freund, T. Ishida, Heterocycles 1990, 30, 1031–1077.
- 103
- 103aT. Kiguchi, C. Hashimoto, I. Ninomiya, Heterocycles 1984, 22, 43–47;
- 103bI. Ninomiya, T. Kiguchi, C. Hashimoto, T. Naito, Chem. Pharm. Bull. 1991, 39, 23–30.
- 104
- 104aI. Ninomiya, C. Hashimoto, T. Kiguchi, Heterocycles 1984, 22, 1035–1038;
- 104bI. Ninomiya, C. Hashimoto, T. Kiguchi, T. Naito, D. H. R. Barton, X. Lusinchi, P. Milliet, J. Chem. Soc. Perkin Trans. 1 1990, 707–713.
- 105I. Ninomiya, N. Habe, T. Kiguchi, T. Naito, J. Chem. Soc. Perkin Trans. 1 1991, 3275–3285.
- 106T. Hjelmgaard, D. Gardette, D. Tanner, D. J. Aitken, Tetrahedron: Asymmetry 2007, 18, 671–678.
- 107F. Bois, D. Gardette, J.-C. Gramain, Tetrahedron Lett. 2000, 41, 8769–8772.
- 108T. Kametani, K. Ujiie, M. Ihara, K. Fukumoto, S.-T. Lu, J. Chem. Soc. Perkin Trans. 1 1976, 1218–1221.
- 109Übersichten:
- 109aT. Damiano, D. Morton, A. Nelson, Org. Biomol. Chem. 2007, 5, 2735–2752;
- 109bJ. Zou, P. S. Mariano, Photochem. Photobiol. Sci. 2008, 7, 393–404.
- 110R. Ling, M. Yoshida, P. S. Mariano, J. Org. Chem. 1996, 61, 4439–4449.
- 111R. Ling, P. S. Mariano, J. Org. Chem. 1998, 63, 6072–6076.
- 112H. Lu, P. S. Mariano, Y.-f. Lam, Tetrahedron Lett. 2001, 42, 4755–4757.
- 113L. Song, E. N. Duesler, P. S. Mariano, J. Org. Chem. 2004, 69, 7284–7293.
- 114Z. Zhao, L. Song, P. S. Mariano, Tetrahedron 2005, 61, 8888–8894.
- 115F. Glarner, B. Acar, I. Etter, T. Damiano, E. A. Acar, G. Bernardinelli, U. Burger, Tetrahedron 2000, 56, 4311–4316.
- 116X. Feng, E. N. Duesler, P. S. Mariano, J. Org. Chem. 2005, 70, 5618–5623.
- 117Y. Kobayashi, H. Miyazaki, M. Shiozaki, J. Org. Chem. 1994, 59, 813–822.
- 118Z. Zhao, P. S. Mariano, Tetrahedron 2006, 62, 7266–7273.
- 119M. Hanaoka, M. Iwasaki, C. Mukai, Tetrahedron Lett. 1985, 26, 917–920.
- 120M. Hanaoka, M. Inoue, S. Sakurai, Y. Shimada, S. Yasuda, Chem. Pharm. Bull. 1982, 30, 1110–1112.
- 121W. A. Ayer, L. M. Browne, Can. J. Chem. 1974, 52, 1352–1360.
- 122A. Greene, P. Crabbé, Tetrahedron Lett. 1975, 16, 2215–2218.
10.1016/S0040-4039(00)72680-3 Google Scholar
- 123Übersichten:
- 123aP. Wessig in CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. ), CRC, Boca Raton, 2004, S. 57/1–57/20;
- 123bP. J. Wagner in CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. ), CRC, Boca Raton, 2004, S. 58/1–58/70;
- 123cP. Margaretha in Methoden Org. Chem. (Houben-Weyl), Vol. E 17e, 4th ed., 1997, S. 71–75;
- 123dP. J. Wagner, B.-S. Park, Org. Photochem. 1991, 11, 227–366.
- 124Die aus Poronia punctata (Linnaeus: Fries) isolierte Naturstoffklasse der Punctaporonine wurde ursprünglich als Punctatine bezeichnet. Um Verwechslungen zu vermeiden, wurde die Umbenennung vorgeschlagen: J. R. Anderson, C. E. Briant, R. L. Edwards, R. P. Mabelis, J. P. Poyser, H. Spencer, A. J. S. Whalley, A. A. Freer, J. Chem. Soc. Chem. Commun. 1986, 984.
- 125
- 125aL. A. Paquette, T. Sugimura, J. Am. Chem. Soc. 1986, 108, 3841–3842;
- 125bT. Sugimura, L. A. Paquette, J. Am. Chem. Soc. 1987, 109, 3017–3024.
- 126G. A. Kraus, L. Chen, J. Am. Chem. Soc. 1990, 112, 3464–3466.
- 127F. Ishibashi, M. Hayashita, M. Okazaki, Y. Shuto, Biosci. Biotechnol. Biochem. 2001, 65, 29–34.
- 128P. De Mayo, R. Suau, J. Chem. Soc. Perkin Trans. 1 1974, 2559–2561.
- 129T. Kozluk, L. Cottier, G. Descotes, Tetrahedron 1981, 37, 1875–1880.
- 130J. C. Gramain, R. Remuson, D. Vallee, J. Org. Chem. 1985, 50, 710–712.
- 131P. De Mayo, R. Suau, J. Am. Chem. Soc. 1974, 96, 6807–6809.
- 132B. Makino, M. Kawai, K. Kito, H. Yamamura, Y. Butsugan, Tetrahedron 1995, 51, 12529–12538.
- 133P. Wessig, J. Teubner, Synlett 2006, 1543–1546.
- 134P. Wessig, O. Muehling, Eur. J. Org. Chem. 2007, 2219–2232.
- 135P. Wessig, C. Glombitza, G. Müller, J. Teubner, J. Org. Chem. 2004, 69, 7582–7591.
- 136J. P. Dittami, F. Xu, H. Qi, M. W. Martin, J. Bordner, D. L. Decosta, J. Kiplinger, P. Reiche, R. Ware, Tetrahedron Lett. 1995, 36, 4197–4200.
- 137J. P. Dittami, F. Xu, H. Qi, M. W. Martin, J. Bordner, D. L. Decosta, J. Kiplinger, P. Reiche, R. Ware, Tetrahedron Lett. 1995, 36, 4201–4204.
- 138Übersichten:
- 138aC. Bohne in CRC Handbook of Organic Photochemistry and Photobiology (Hrsg.: ), CRC, Boca Raton, 1995, S. 417–448;
- 138bD. S. Weiss, Org. Photochem. 1981, 5, 347–471.
- 139A. Natarajan, D. Ng, Z. Yang, M. A. Garcia-Garibay, Angew. Chem. 2007, 119, 6605–6607; Angew. Chem. Int. Ed. 2007, 46, 6485–6487.
- 140D. Ng, Z. Yang, M. A. Garcia-Garibay, Org. Lett. 2004, 6, 645–647.
- 141Eine Zusammenfassung von Naturstoffsynthesen, in denen die Photoeliminierung von CO2 oder N2 angewendet wurde, findet sich in einem kürzlich erschienenen Übersichtsartikel: S. Shiraki, M. A. Garcia-Garibay in Handbook of Synthetic Photochemistry (Hrsg.: ), Wiley-VCH, Weinheim, 2010, S. 25–66; weitere Übersicht über die Photoextrusion kleiner Moleküle: R. S. Givens, Org. Photochem. 1981, 5, 227–346.
- 142C.-H. Lin, Y.-L. Su, H.-M. Tai, Heterocycles 2006, 68, 771–777.
- 143E. Van der Eycken, J. Van der Eycken, M. Vandewalle, J. Chem. Soc. Chem. Commun. 1985, 1719–1720.
- 144P. Callant, P. Storme, E. Van der Eycken, M. Vandewalle, Tetrahedron Lett. 1983, 24, 5797–5800.
- 145H.-M. Tai, M.-H. Huang, C.-C. Yang, J. Chin. Chem. Soc. 2003, 50, 441–444.
- 146N. Itagaki, Y. Iwabuchi, Chem. Commun. 2007, 1175–1176.
- 147
- 147aH. G. Davies, S. M. Roberts, B. J. Wakefield, J. A. Winders, J. Chem. Soc. Chem. Commun. 1985, 1166–1168;
- 147bG. Dormán, S. M. Roberts, B. J. Wakefield, J. A. Winders, J. Chem. Soc. Perkin Trans. 1 1989, 1543–1544.
- 148I. C. Cotterill, R. Jaouhari, G. Dorman, S. M. Roberts, F. Scheinmann, B. J. Wakefield, J. Chem. Soc. Perkin Trans. 1 1991, 2505–2512.
- 149S. S. Rahman, B. J. Wakefield, S. M. Roberts, M. D. Dowle, J. Chem. Soc. Chem. Commun. 1989, 303–304.
- 150S. Butt, H. G. Davies, M. J. Dawson, G. C. Lawrence, S. Jeff Leaver, M. Roberts, M. K. Turner, B. J. Wakefield, W. F. Wall, A. Winders, J. Chem. Soc. Perkin Trans. 1 1987, 903–907.
- 151G. A. Molander, D. J. St. Jean, J. Haas, J. Am. Chem. Soc. 2004, 126, 1642–1643.
- 152
- 152aR. F. Newton, D. P. Reynolds, N. M. Crossland, D. R. Kelly, S. M. Roberts, J. Chem. Soc. Chem. Commun. 1979, 683–684;
- 152bC. C. Howard, R. F. Newton, D. P. Reynolds, A. H. Wadsworth, D. R. Kelly, S. M. Roberts, J. Chem. Soc. Perkin Trans. 1 1980, 852–857.
- 153M. C. Pirrung, C. V. DeAmicis, Tetrahedron Lett. 1988, 29, 159–162.
- 154Übersicht: V. Singh in CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. ), CRC, Boca Raton, 2004, S. 79/1–79/34.
- 155
- 155aT. Uyehara, T. Furuta, Y. Kabasawa, J. Yamada, T. Kato, J. Chem. Soc. Chem. Commun. 1986, 539–540;
- 155bT. Uyehara, T. Furuta, Y. Kabasawa, J. Yamada, T. Kato, Y. Yamamoto, J. Org. Chem. 1988, 53, 3669–3673.
- 156
- 156aT. Uyehara, Y. Kabasawa, T. Kato, T. Furuta, Tetrahedron Lett. 1985, 26, 2343–2346;
- 156bT. Uyehara, Y. Kabasawa, T. Kato, Bull. Chem. Soc. Jpn. 1986, 59, 2521–2528.
- 157T. Uyehara, T. Furuta, M. Akamatsu, T. Kato, Y. Yamamoto, J. Org. Chem. 1989, 54, 5411–5413.
- 158L. F. Hsu, C. P. Chang, M. C. Li, N. C. Chang, J. Org. Chem. 1993, 58, 4756–4757.
- 159Übersichten:
- 159aV. J. Rao, A. G. Griesbeck in Molecular and Supramolecular Photochemistry, Vol. 12 (Hrsg.: ), Marcel Dekker, New York, 2005, S. 189–210;
- 159bV. Singh in CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. ), CRC, Boca Raton, 2004, S. 78/1–78/34;
- 159cM. Demuth, Org. Photochem. 1991, 11, 37–109;
- 159dD. I. Schuster in Rearrangements in Ground and Excited States (Hrsg.: ), Academic Press, New York, 1980, S. 232–279.
- 160
- 160aK. E. Stevens, P. Yates, J. Chem. Soc. Chem. Commun. 1980, 990–991;
- 160bP. Yates, K. E. Stevens, Tetrahedron 1981, 37, 4401–4410.
- 161
- 161aG. Stork, F. H. Clarke, Jr., J. Am. Chem. Soc. 1955, 77, 1072–1073;
- 161bG. Stork, F. H. Clarke, Jr., J. Am. Chem. Soc. 1961, 83, 3114–3125.
- 162Übersichten:
- 162aM. Demuth, Pure Appl. Chem. 1986, 58, 1233–1238;
- 162bM. Demuth in Modern Synthetic Methods, Vol. 4 (Hrsg.: ), Springer, Berlin, 1986, S. 89–124;
10.1007/978-3-642-82805-8_3 Google Scholar
- 162cM. Demuth, W. Hinsken, Angew. Chem. 1985, 97, 974–976; Angew. Chem. Int. Ed. Engl. 1985, 24, 973–975;
- 162dM. Demuth, K. Schaffner, Angew. Chem. 1982, 94, 809–825; Angew. Chem. Int. Ed. Engl. 1982, 21, 820–836.
- 163M. Demuth, S. Chandrasekehar, K. Schaffner, J. Am. Chem. Soc. 1984, 106, 1092–1095.
- 164P. Ritterskamp, M. Demuth, K. Schaffner, J. Org. Chem. 1984, 49, 1155–1158.
- 165Synthese des strukturell verwandten (±)-Forsythid-Aglucondimethylesters: C.-C. Liao, C.-P. Wei, Tetrahedron Lett. 1989, 30, 2255–2256.
- 166
- 166aM. Demuth, P. Ritterskamp, K. Schaffner, Helv. Chim. Acta 1984, 67, 2023–2027;
- 166bM. Demuth, P. Ritterskamp, E. Weigt, K. Schaffner, J. Am. Chem. Soc. 1986, 108, 4149–4154.
- 167
- 167aV. Singh, S. Q. Alam, Chem. Commun. 1999, 2519–2520;
- 167bV. Singh, B. Samanta, V. V. Kane, Tetrahedron 2000, 56, 7785–7795;
- 167cV. Singh, S. Prathap, M. Porinchu, J. Org. Chem. 1998, 63, 4011–4017;
- 167dV. Singh, P. Vedantham, P. K. Sahu, Tetrahedron Lett. 2002, 43, 519–522;
- 167eV. Singh, P. Vedantham, P. K. Sahu, Tetrahedron 2004, 60, 8161–8169;
- 167fV. Singh, D. K. Tosh, S. M. Mobin, Tetrahedron Lett. 2004, 45, 1729–1732;
- 167gV. Singh, S. Pal, D. K. Tosh, S. M. Mobin, Tetrahedron 2007, 63, 2446–2454;
- 167hV. Singh, B. Samanta, Tetrahedron Lett. 1999, 40, 383–386.
- 168D.-S. Hsu, Y.-Y. Chou, Y.-S. Tung, C.-C. Liao, Chem. Eur. J. 2010, 16, 3121–3131.
- 169
- 169aT. A. Reekie, K. A. B. Austin, M. G. Banwell, A. C. Willis, Aust. J. Chem. 2008, 61, 94–106;
- 169bM. G. Banwell, A. J. Edwards, G. J. Harfoot, K. A. Jolliffe, J. Chem. Soc. Perkin Trans. 1 2002, 2439–2441;
- 169cM. G. Banwell, A. J. Edwards, G. J. Harfoot, K. A. Jolliffe, Tetrahedron 2004, 60, 535–547;
- 169dK. A. B. Austin, M. G. Banwell, G. J. Harfoot, A. C. Willis, Tetrahedron Lett. 2006, 47, 7381–7384;
- 169eM. G. Banwell, K. A. B. Austin, A. C. Willis, Tetrahedron 2007, 63, 6388–6403.
- 170
- 170aU. Eder, G. Sauer, R. Wiechert, Angew. Chem. 1971, 83, 492–493;
10.1002/ange.19710831307 Google ScholarAngew. Chem. Int. Ed. Engl. 1971, 10, 496–497;
- 170bZ. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615–1621.
- 171M. Demuth, W. Hinsken, Helv. Chim. Acta 1988, 71, 569–576.
- 172
- 172aG. Mehta, D. Subrahmanyam, J. Chem. Soc. Chem. Commun. 1985, 768–769;
- 172bG. Mehta, D. Subrahmanyam, J. Chem. Soc. Perkin Trans. 1 1991, 395–401.
- 173T. Uyehara, T. Murayama, K. Sakai, K. Onda, M. Ueno, T. Sato, Bull. Chem. Soc. Jpn. 1998, 71, 231–242.
- 174
- 174aR. S. Grewal, P. C. Hayes, J. F. Sawyer, P. Yates, J. Chem. Soc. Chem. Commun. 1987, 1290–1292;
- 174bP. Yates, R. S. Grewal, P. C. Hayes, J. F. Sawyer, Can. J. Chem. 1988, 66, 2805–2815.
- 175Lit. [168].
- 176C.-F. Yen, C.-C. Liao, Angew. Chem. 2002, 114, 4264–4267;
10.1002/1521-3757(20021104)114:21<4264::AID-ANGE4264>3.0.CO;2-M Google ScholarAngew. Chem. Int. Ed. 2002, 41, 4090–4093.10.1002/1521-3773(20021104)41:21<4090::AID-ANIE4090>3.0.CO;2-# CAS PubMed Web of Science® Google Scholar
- 177S. A. Monti, S. D. Larsen, J. Org. Chem. 1978, 43, 2282–2284.
- 178Übersichten:
- 178aD. Armesto, M. J. Ortiz, A. R. Agarrabeitia in Molecular and Supramolecular Photochemistry, Vol. 12 (Hrsg.: ), Marcel Dekker, New York, 2005, S. 161–187;
- 178bH. E. Zimmerman, D. Armesto, Chem. Rev. 1996, 96, 3065–3112;
- 178cH. E. Zimmerman, Org. Photochem. 1991, 11, 1–36;
- 178dD. Döpp, H. E. Zimmerman in Methoden Org. Chem. (Houben-Weyl), Vol. 5a, 4th ed., 1975, S. 413–432.
- 179S. A. Look, W. Fenical, D. Van Engen, J. Clardy, J. Am. Chem. Soc. 1984, 106, 5026–5027.
- 180
- 180aC. Ireland, P. J. Scheuer, Science 1979, 205, 922–923;
- 180bD. R. Zuidema, A. K. Miller, D. Trauner, P. B. Jones, Org. Lett. 2005, 7, 4959–4962.
- 181
- 181aP. Baeckström, J. Chem. Soc. Chem. Commun. 1976, 476–477;
- 181bP. Baeckström, Tetrahedron 1978, 34, 3331–3335;
- 181cM. J. Bullivant, G. Pattenden, J. Chem. Soc. Perkin Trans. 1 1976, 256–258.
- 182D. Armesto, M. G. Gallego, W. M. Horspool, A. R. Agarrabeitia, Tetrahedron 1995, 51, 9223–9240.
- 183Übersicht: M. A. Miranda, F. Galindo in CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. ), CRC, Boca Raton, 2004, S. 42/1–42/11.
- 184M. Zissler, J. Piel, S. Lochbrunner, E. Riedle, A. Spiegel, T. Bach, J. Chem. Phys. 2004, 120, 11634–11639, zit. Lit.
- 185K. Okada, R. Suzuki, T. Yokota, Biosci. Biotechnol. Biochem. 1999, 63, 257–260.
- 186
- 186aT. Magauer, H. J. Martin, J. Mulzer, Angew. Chem. 2009, 121, 6148–6152; Angew. Chem. Int. Ed. 2009, 48, 6032–6036;
- 186bT. Magauer, H. J. Martin, J. Mulzer, Chem. Eur. J. 2010, 16, 507–519.
- 187D. Taub, C. H. Kuo, H. L. Slates, N. L. Wendler, Tetrahedron 1963, 19, 1–17.
- 188A. S. Kende, J. L. Belletire, E. L. Hume, Tetrahedron Lett. 1973, 14, 2935–2938.
10.1016/S0040-4039(01)96286-0 Google Scholar
- 189
- 189aT. Kato, N. Katagiri, J. Nakano, H. Kawamura, J. Chem. Soc. Chem. Commun. 1977, 645–646;
- 189bN. Katagiri, J. Nakano, T. Kato, J. Chem. Soc. Perkin Trans. 1 1981, 2710–2716.
- 190F. Farina, R. Martinez-Utrilla, M. C. Paredes, Tetrahedron 1982, 38, 1531–1537.
- 191M. A. Miranda, J. Primo, R. Tormos, Heterocycles 1991, 32, 1159–1666.
- 192R. Suau, M. Valpuesta, G. Torres, Tetrahedron Lett. 1995, 36, 1315–1318.
- 193J. Gràcia, J. Bonjoch, N. Casamitjana, M. Amat, J. Bosch, J. Chem. Soc. Chem. Commun. 1991, 614–615.
- 194J. Bonjoch, J. Catena, N. Valls, J. Org. Chem. 1996, 61, 7106–7115.
- 195Übersicht: M. Oelgemöller, J. Mattay in CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. ), CRC, Boca Raton, 2004, S. 88/1–88/45.
- 196K. Maruyama, Y. Naruta, Chem. Lett. 1977, 6, 847–850.
- 197H. Trommsdorff, Ann. Chem. Pharm. 1834, 11, 190–207.
10.1002/jlac.18340110207 Google Scholar
- 198Übersicht: G. Blay in CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. ), CRC, Boca Raton, 2004, S. 80/1–80/21.
- 199
- 199aS. Cannizzaro, G. Fabris, Chem. Ber. 1886, 19, 2260–2265;
10.1002/cber.188601902140 Google Scholar
- 199bD. H. R. Barton, P. de Mayo, M. Shafiq, J. Chem. Soc. 1957, 929–935;
- 199cD. H. R. Barton, J. E. D. Levisalles, J. T. Pinhey, J. Chem. Soc. 1962, 3472–3482.
- 200H. E. Zimmerman, D. I. Schuster, J. Am. Chem. Soc. 1962, 84, 4527–4540.
- 201
- 201aE. H. White, J. N. Marx, J. Am. Chem. Soc. 1967, 89, 5511–5513;
- 201bJ. N. Marx, E. H. White, Tetrahedron 1969, 25, 2117–2120.
- 202M. T. Edgar, A. E. Greene, P. Crabbe, J. Org. Chem. 1979, 44, 159–160.
- 203A. E. Greene, J. Am. Chem. Soc. 1980, 102, 5337–5343.
- 204A. E. Greene, M. T. Edgar, J. Org. Chem. 1989, 54, 1468–1470.
- 205P. Delair, N. Kann, A. E. Greene, J. Chem. Soc. Perkin Trans. 1 1994, 1651–1652.
- 206G. Blay, V. Bargues, L. Cardona, B. García, J. R. Pedro, Tetrahedron 2001, 57, 9719–9725.
- 207G. Blay, L. Cardona, B. García, L. Lahoz, J. R. Pedro, J. Org. Chem. 2001, 66, 7700–7705.
- 208E. F. Makiyi, R. F. M. Frade, T. Lebl, E. G. Jaffray, S. E. Cobb, A. L. Harvey, A. M. Z. Slawin, R. T. Hay, N. J. Westwood, Eur. J. Org. Chem. 2009, 5711–5715.
- 209G. Blay, V. Bargues, L. Cardona, A. M. Collado, B. García, M. C. Muñoz, J. R. Pedro, J. Org. Chem. 2000, 65, 2138–2144.
- 210G. Blay, V. Bargues, L. Cardona, B. Garcia, J. R. Pedro, J. Org. Chem. 2000, 65, 6703–6707.
- 211
- 211aJ. A. Marshall, P. C. Johnson, J. Org. Chem. 1970, 35, 192–196;
- 211bD. Caine, C.-Y. Chu, S. L. Graham, J. Org. Chem. 1980, 45, 3790–3797.
- 212D. Caine, P. F. Ingwalson, J. Org. Chem. 1972, 37, 3751–3752.
- 213D. Caine, H. Deutsch, J. Am. Chem. Soc. 1978, 100, 8030–8031.
- 214
- 214aD. Caine, F. N. Tuller, J. Am. Chem. Soc. 1971, 93, 6311–6312;
- 214bD. Caine, F. N. Tuller, J. Org. Chem. 1973, 38, 3663–3670.
- 215D. Caine, A. S. Frobese, Tetrahedron Lett. 1977, 18, 3107–3110.
10.1016/S0040-4039(01)83172-5 Google Scholar
- 216K. Yakushijin, H. Furukawa, A. T. McPhail, Chem. Pharm. Bull. 1984, 32, 23–30.
- 217X. Lei, M. Dai, Z. Hua, S. J. Danishefsky, Tetrahedron Lett. 2008, 49, 6383–6385.
- 218
- 218aJ. J. Hurst, G. H. Whitham, Proc. Chem. Soc. 1959, 160;
- 218bJ. J. Hurst, G. H. Whitham, J. Chem. Soc. 1960, 2864–2869.
- 219Y. Uchio, Tetrahedron 1978, 34, 2893–2899.
- 220A. E. Greene, J.-C. Muller, G. Ourisson, Tetrahedron Lett. 1971, 12, 4147–4149.
10.1016/S0040-4039(01)97485-4 Google Scholar
- 221
- 221aH. R. Sonawane, B. S. Nanjundiah, M. U. Kumar, Tetrahedron Lett. 1984, 25, 2245–2246;
- 221bH. R. Sonawane, V. G. Naik, N. S. Bellur, V. G. Shah, P. C. Purohit, M. U. Kumar, D. G. Kulltarni, J. R. Ahuja, Tetrahedron 1991, 47, 8259–8276.
- 222
- 222aT. Uyehara, K. Ogata, J.-i. Yamada, T. Kato, J. Chem. Soc. Chem. Commun. 1983, 17–18;
- 222bT. Uyehara, J.-i. Yamada, K. Ogata, T. Kato, Bull. Chem. Soc. Jpn. 1985, 58, 211–216.
- 223G. Majetich, J. Yu, Org. Lett. 2007, 9, 89–91.
- 224H. G. Theuns, G. F. La Vos, M. C. ten Noever de Brauw, C. A. Salemink, Tetrahedron Lett. 1984, 25, 4161–4162.
- 225Übersichten:
- 225aJ. L. Segura, N. Martin, Chem. Rev. 1999, 99, 3199–3246;
- 225bJ. L. Charlton, M. M. Alauddin, Tetrahedron 1987, 43, 2873–2889.
- 226Übersicht: P. G. Sammes, Tetrahedron 1976, 32, 405–422.
- 227
- 227aK. C. Nicolaou, D. Gray, Angew. Chem. 2001, 113, 783–785;
10.1002/1521-3757(20010216)113:4<783::AID-ANGE7830>3.0.CO;2-X Google ScholarAngew. Chem. Int. Ed. 2001, 40, 761–763;10.1002/1521-3773(20010216)40:4<761::AID-ANIE7610>3.0.CO;2-0 CAS PubMed Web of Science® Google Scholar
- 227bK. C. Nicolaou, D. L. F. Gray, J. Am. Chem. Soc. 2004, 126, 607–612.
- 228
- 228aG. Quinkert, W.-D. Weber, U. Schwartz, G. Dürner, Angew. Chem. 1980, 92, 1060–1062; Angew. Chem. Int. Ed. Engl. 1980, 19, 1027–1029;
- 228bG. Quinkert, U. Schwartz, H. Stark, W.-D. Weber, H. Baier, F. Adam, G. Dürner, Angew. Chem. 1980, 92, 1062–1063; Angew. Chem. Int. Ed. Engl. 1980, 19, 1029–1030;
- 228cG. Quinkert, W.-D. Weber, U. Schwartz, H. Stark, H. Baier, G. Dürner, Liebigs Ann. Chem. 1981, 2335–2371;
- 228dG. Quinkert, U. Schwartz, H. Stark, W.-D. Weber, F. Adam, H. Baier, G. Frank, G. Dürner, Liebigs Ann. Chem. 1982, 1999–2040;
- 228eG. Quinkert, H. Stark, Angew. Chem. 1983, 95, 651–669; Angew. Chem. Int. Ed. Engl. 1983, 22, 637–655.
- 229
- 229aG. H. Douglas, J. M. H. Graves, D. Hartley, G. A. Hughes, B. J. McLoughlin, J. Siddall, H. Smith, J. Chem. Soc. 1963, 5072–5094;
- 229b W. S. Johnson, D. K. Banerjee, W. P. Schneider, C. D. Gutsche, W. E. Shelberg, L. J. Chinn, J. Am. Chem. Soc. 1952, 74, 2832–2849.
- 230
- 230aK. C. Nicolaou, D. Gray, J. Tae, Angew. Chem. 2001, 113, 3791–3795;
10.1002/1521-3757(20011001)113:19<3791::AID-ANGE3791>3.0.CO;2-J Google ScholarAngew. Chem. Int. Ed. 2001, 40, 3679–3683;10.1002/1521-3773(20011001)40:19<3679::AID-ANIE3679>3.0.CO;2-T CAS PubMed Web of Science® Google Scholar
- 230bK. C. Nicolaou, D. L. F. Gray, J. Tae, J. Am. Chem. Soc. 2004, 126, 613–627.
- 231D. H. R. Barton, P. D. Magnus, T. Haase, J. Chem. Soc. C 1971, 2215–2225.
- 232D. H. R. Barton, D. L. J. Clive, P. D. Magnus, G. Smith, J. Chem. Soc. C 1971, 2193–2203.
- 233G. A. Kraus, Y. Wu, J. Org. Chem. 1992, 57, 2922–2925.
- 234
- 234aS. Prabhakar, A. M. Lobo, I. M. C. Oliveira, J. Chem. Soc. Chem. Commun. 1977, 419–420;
- 234bS. Prabhakar, A. M. Lobo, M. R. Tavares, I. M. C. Oliveira, J. Chem. Soc. Perkin Trans. 1 1981, 1273–1277.
- 235Übersichten:
- 235aO. Piva in CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. ), CRC, Boca Raton, 2004, S. 70/1–70/18;
- 235bJ.-P. Pete in CRC Handbook of Organic Photochemistry and Photobiology (Hrsg.: ), CRC, Boca Raton, 1995, S. 593–617.
- 236O. Piva, J. Org. Chem. 1995, 60, 7879–7883.
- 237O. Piva, J.-P. Pete, Tetrahedron Lett. 1990, 31, 5157–5160.
- 238D. A. Lombardo, A. C. Weedon, Tetrahedron Lett. 1986, 27, 5555–5558.
- 239S. Faure, J. D. Connolly, C. O. Fakunle, O. Piva, Tetrahedron 2000, 56, 9647–9653.
- 240H. Salim, O. Piva, J. Org. Chem. 2009, 74, 2257–2260.
- 241
- 241aE. Paternò, G. Chieffi, Gazz. Chim. Ital. 1909, 39, 341–361;
- 241bG. Büchi, C. G. Inman, E. S. Lipinsky, J. Am. Chem. Soc. 1954, 76, 4327–4331.
- 242Übersichten:
- 242aM. Abe in Handbook of Synthetic Photochemistry (Hrsg.: ), Wiley-VCH, Weinheim, 2010, S. 217–239;
- 242bA. G. Griesbeck in Molecular and Supramolecular Photochemistry, Vol. 12 (Hrsg.: ), Marcel Dekker, New York, 2005, S. 89–139;
- 242cA. G. Griesbeck, S. Bondock in CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. ), CRC, Boca Raton, 2004, S. 59/1–59/19;
- 242dA. G. Griesbeck, S. Bondock in CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. ), CRC, Boca Raton, 2004, S. 60/1–60/21;
- 242eT. Bach, Synlett 2000, 1699–1707;
- 242fA. G. Griesbeck, M. Fiege in Molecular and Supramolecular Photochemistry, Vol. 6 (Hrsg.: ), Marcel Dekker, New York, 2000, S. 33–100;
- 242gT. Bach, Synthesis 1998, 683–703;
- 242hJ. Mattay, R. Conrads, R. Hoffmann in Methoden Org. Chem. (Houben-Weyl) Vol. E 21c, 4th ed., 1995, S. 3133–3178;
- 242iJ. A. Porco, S. L. Schreiber in Comprehensive Organic Synthesis, Vol. 5 (Hrsg.: ), Pergamon, Oxford, 1991, S. 151–192;
- 242jM. Demuth, G. Mikhail, Synthesis 1989, 145–162;
- 242kH. A. J. Carless in Synthetic Organic Photochemistry (Hrsg.: ), Plenum, New York, 1984, S. 425–487;
10.1007/978-1-4613-2681-6_8 Google Scholar
- 242lG. Jones II, Org. Photochem. 1981, 5, 1–123;
- 242mD. R. Arnold, Adv. Photochem. 1968, 6, 301–426.
- 243T. Bach, J. Schröder, Liebigs Ann. 1997, 2265–2267.
- 244R. Hambalek, G. Just, Tetrahedron Lett. 1990, 31, 5445–5448.
- 245
- 245aS. L. Schreiber, Science 1985, 227, 857–863;
- 245bsiehe auch: R. A. Aungst, Jr., R. L. Funk, J. Am. Chem. Soc. 2001, 123, 9455–9456.
- 246S. L. Schreiber, A. H. Hoveyda, J. Am. Chem. Soc. 1984, 106, 7200–7202.
- 247S. L. Schreiber, K. Satake, J. Am. Chem. Soc. 1984, 106, 4186–4188.
- 248A. G. Griesbeck, H. Mauder, S. Stadtmüller, Acc. Chem. Res. 1994, 27, 70–75.
- 249A. Nehrings, H.-D. Scharf, J. Runsink, Angew. Chem. 1985, 97, 882–883; Angew. Chem. Int. Ed. Engl. 1985, 24, 877–878.
- 250
- 250aH. Buschmann, H.-D. Scharf, N. Hoffmann, P. Esser, Angew. Chem. 1991, 103, 480–518; Angew. Chem. Int. Ed. Engl. 1991, 30, 477–515;
- 250bH. Koch, J. Runsink, H.-D. Scharf, Tetrahedron Lett. 1983, 24, 3217–3220.
- 251T. R. Hoye, W. S. Richardson, J. Org. Chem. 1989, 54, 688–693.
- 252T. Bach, J. Schröder, Tetrahedron Lett. 1997, 38, 3707–3710.
- 253
- 253aT. Bach, Liebigs Ann. 1997, 1627–1634;
- 253bT. Bach, Tetrahedron Lett. 1994, 35, 1855–1858;
- 253cD. R. Morton, R. A. Morge, J. Org. Chem. 1978, 43, 2093–2101.
- 254
- 254aT. Bach, H. Brummerhop, Angew. Chem. 1998, 110, 3577–3579;
10.1002/(SICI)1521-3757(19981217)110:24<3577::AID-ANGE3577>3.0.CO;2-3 Web of Science® Google ScholarAngew. Chem. Int. Ed. 1998, 37, 3400–3402;10.1002/(SICI)1521-3773(19981231)37:24<3400::AID-ANIE3400>3.0.CO;2-3 CAS Web of Science® Google Scholar
- 254bT. Bach, H. Brummerhop, K. Harms, Chem. Eur. J. 2000, 6, 3838–3848.
10.1002/1521-3765(20001016)6:20<3838::AID-CHEM3838>3.0.CO;2-1 CAS PubMed Web of Science® Google Scholar
- 255G. Jones II, M. A. Acquadro, M. A. Carmody, J. Chem. Soc. Chem. Commun. 1975, 206–207.
- 256V. H. Rawal, C. Dufour, J. Am. Chem. Soc. 1994, 116, 2613–2614.
- 257
- 257aV. H. Rawal, C. Dufour, A. Eschbach, J. Chem. Soc. Chem. Commun. 1994, 1797–1798;
- 257bV. H. Rawal, A. Eschbach, C. Dufour, S. Iwasa, Pure Appl. Chem. 1996, 68, 675–678.
- 258V. H. Rawal, A. Fabré, S. Iwasa, Tetrahedron Lett. 1995, 36, 6851–6854.
- 259C. A. Dvorak, V. H. Rawal, Chem. Commun. 1997, 2381–2382.
- 260T. J. Reddy, V. H. Rawal, Org. Lett. 2000, 2, 2711–2712.
- 261R. J. Boxall, L. Ferris, R. S. Grainger, Synlett 2004, 2379–2381.
- 262Übersichten:
- 262aJ. P. Hehn, C. Müller, T. Bach in Handbook of Synthetic Photochemistry (Hrsg.: ), Wiley-VCH, Weinheim, 2010, S. 171–215;
- 262bJ. Iriondo-Alberdi, M. F. Greaney, Eur. J. Org. Chem. 2007, 4801–4815;
- 262cS. A. Fleming in Molecular and Supramolecular Photochemistry, Vol. 12 (Hrsg.: ), Marcel Dekker, New York, 2005, S. 141–160;
- 262dP. Margaretha in Molecular and Supramolecular Photochemistry, Vol. 12 (Hrsg.: ), Marcel Dekker, New York, 2005, S. 211–237;
- 262eJ. P. Pete in CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. ), CRC, Boca Raton, 2004, S. 71/1–71/14;
- 262fW. M. Horspool, Photochemistry 2001, 32, 74–116;
- 262gLit. [240g];
- 262hS. A. Fleming, C. L. Bradford, J. J. Gao in Molecular and Supramolecular Photochemistry, Vol. 1 (Hrsg.: ), Marcel Dekker, New York, 1997, S. 187–244;
- 262iJ.-P. Pete, Adv. Photochem. 1996, 21, 135–216;
- 262jJ. Mattay, R. Conrads, R. Hoffmann in Methoden Org. Chem. (Houben-Weyl), Vol. E 21c, 4th ed., 1995, S. 3085–3132;
- 262kM. T. Crimmins, T. L. Reinhold, Org. React. 1993, 44, 297–588;
- 262lM. T. Crimmins in Comprehensive Organic Synthesis, Vol. 5 (Hrsg.: ), Pergamon, Oxford, 1991, S. 123–150;
10.1016/B978-0-08-052349-1.00122-0 Google Scholar
- 262mLit. [240j];
- 262nD. Becker, N. Haddad, Org. Photochem. 1989, 10, 1–162;
- 262oM. T. Crimmins, Chem. Rev. 1988, 88, 1453–1473;
- 262pS. V. Baldwin, Org. Photochem. 1981, 5, 123–225;
- 262qP. G. Bauslaugh, Synthesis 1970, 287–300.
- 263
- 263aD. I. Schuster in CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. ), CRC, Boca Raton, 2004, S. 72/1–72/24;
- 263bD. I. Schuster, G. Lem, N. A. Kaprinidis, Chem. Rev. 1993, 93, 3–22.
- 264Übersichten:
- 264aS. Ghosh in CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. ), CRC, Boca Raton, 2004, S. 18/1–18/24;
- 264bP. Margaretha in Methoden Org. Chem. (Houben-Weyl), Vol. E 17e, 4th ed., 1997, S. 159–162;
- 264cR. G. Salomon, Tetrahedron 1983, 39, 485–575.
- 265E. Marotta, P. Righi, G. Rosini, Org. Process Res. Dev. 1999, 3, 206–219.
- 266
- 266aJ. H. Tumlinson, D. D. Hardee, R. C. Gueldner, A. C. Thompson, P. A. Hedin, J. P. Minyard, Science 1969, 166, 1010–1012;
- 266bJ. H. Tumlinson, R. C. Gueldner, D. D. Hardee, A. C. Thompson, P. A. Hedin, J. P. Minyard, J. Org. Chem. 1971, 36, 2616–2621.
- 267R. L. Cargill, B. W. Wright, J. Org. Chem. 1975, 40, 120–122.
- 268R. Zurflüh, L. Dunham, V. Spain, J. Siddall, J. Am. Chem. Soc. 1970, 92, 425–427.
- 269
- 269aD. P. G. Hamon, K. L. Tuck, Tetrahedron Lett. 1999, 40, 7569–7572;
- 269bD. P. G. Hamon, K. L. Tuck, J. Org. Chem. 2000, 65, 7839–7846.
- 270
- 270aR. C. Gueldner, A. C. Thompson, P. A. Hedin, J. Org. Chem. 1972, 37, 1854–1856;
- 270bH. Kosugi, S. Sekiguchi, R.-i. Sekita, H. Uda, Bull. Chem. Soc. Jpn. 1976, 49, 520–528.
- 271F. X. Webster, R. M. Silverstein, J. Org. Chem. 1986, 51, 5226–5231.
- 272N. Hoffmann, H.-D. Scharf, Liebigs Ann. Chem. 1991, 1273–1277.
- 273
- 273aR. Alibés, J. L. Bourdelande, J. Font, Tetrahedron Lett. 1993, 34, 7455–7458;
- 273bR. Alibés, J. L. Bourdelande, J. Font, T. Parella, Tetrahedron 1996, 52, 1279–1292.
- 274
- 274aP. de March, M. Figueredo, J. Font, J. Raya, Org. Lett. 2000, 2, 163–165;
- 274bP. de March, M. Figueredo, J. Font, J. Raya, A. Alvarez-Larena, J. F. Piniella, J. Org. Chem. 2003, 68, 2437–2447.
- 275A. I. Meyers, S. A. Fleming, J. Am. Chem. Soc. 1986, 108, 306–307.
- 276G. Rosini, E. Marotta, M. Petrini, R. Ballini, Tetrahedron 1985, 41, 4633–4638.
- 277
- 277aG. Rosini, M. Geier, E. Marotta, M. Petrini, R. Ballini, Tetrahedron 1986, 42, 6027–6032;
- 277bK. Langer, J. Mattay, A. Heidbreder, M. Möller, Liebigs Ann. Chem. 1992, 257–260.
- 278J. Panda, S. Ghosh, S. Ghosh, ARKIVOC 2001, VIII, 146–153.
10.3998/ark.5550190.0002.816 Google Scholar
- 279K. Langer, J. Mattay, J. Org. Chem. 1995, 60, 7256–7266.
- 280
- 280aG. Rosini, P. Carloni, M. C. Iapalucci, E. Marotta, Tetrahedron: Asymmetry 1990, 1, 751–758;
- 280bG. Rosini, E. Marotta, A. Raimondi, P. Righi, Tetrahedron: Asymmetry 1991, 2, 123–138.
- 281
- 281aR. Alibés, P. de March, M. Figueredo, J. Font, M. Racamonde, T. Parella, Org. Lett. 2004, 6, 1449–1452;
- 281bM. Racamonde, R. Alibés, M. Figueredo, J. Font, P. de March, J. Org. Chem. 2008, 73, 5944–5952.
- 282K. Mori, M. Sasaki, Tetrahedron Lett. 1979, 20, 1329–1332.
10.1016/S0040-4039(01)86140-2 Google Scholar
- 283J. D. White, M. A. Avery, J. P. Carter, J. Am. Chem. Soc. 1982, 104, 5486–5489.
- 284E. J. Corey, R. N. Mita, H. Uda, J. Am. Chem. Soc. 1964, 86, 485–492.
- 285V. B. Birman, X.-T. Jiang, Org. Lett. 2004, 6, 2369–2371.
- 286
- 286aP. S. Baran, A. L. Zografos, D. P. O’Malley, J. Am. Chem. Soc. 2004, 126, 3726–3727;
- 286bP. S. Baran, K. Li, D. P. O’Malley, C. Mitsos, Angew. Chem. 2006, 118, 255–258;
10.1002/ange.200503374 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 249–252;
- 286cD. P. O’Malley, K. Li, M. Maue, A. L. Zografos, P. S. Baran, J. Am. Chem. Soc. 2007, 129, 4762–4775.
- 287L. A. Paquette, H.-S. Lin, M. J. Coghlan, Tetrahedron Lett. 1987, 28, 5017–5020.
- 288H. Takeshita, H. Iwabuchi, I. Kouno, Chem. Lett. 1979, 649–652.
- 289
- 289aB. Basler, S. Brandes, A. Spiegel, T. Bach, Top. Curr. Chem. 2005, 243, 1–42;
- 289bE. Piers, A. Orellana, Synthesis 2001, 2138–2142;
- 289cS. Fietz-Razavian, S. Schulz, I. Dix, P. G. Jones, Chem. Commun. 2001, 2154–2155;
- 289dG. Mehta, K. Srinivas, Tetrahedron Lett. 1999, 40, 4877–4880.
- 290
- 290aL. Moens, M. M. Baizer, R. D. Little, J. Org. Chem. 1986, 51, 4497–4498;
- 290bG. M. Strunz, R. Bethell, M. T. Dumas, N. Boyonosk, Can. J. Chem. 1997, 75, 742–753;
- 290cG. Mehta, K. Sreenivas, Tetrahedron Lett. 2002, 43, 703–706;
- 290dN. El-Hachach, R. Gerke, M. Noltemeyer, L. Fitjer, Tetrahedron 2009, 65, 1040–1047.
- 291L. A. Paquette, H. S. Lin, B. P. Gunn, M. J. Coghlan, J. Am. Chem. Soc. 1988, 110, 5818–5826.
- 292N. El-Hachach, M. Fischbach, R. Gerke, L. Fitjer, Tetrahedron 1999, 55, 6119–6128.
- 293R. W. Guthrie, Z. Valenta, K. Wiesner, Tetrahedron Lett. 1966, 7, 4645–4654.
10.1016/S0040-4039(00)70092-X Google Scholar
- 294K. Wiesner, L. Poon, I. Jirkovský, M. Fishman, Can. J. Chem. 1969, 47, 433–444.
- 295
- 295aD. E. Ward, Y. Gai, Q. Qiao, Org. Lett. 2000, 2, 2125–2127;
- 295bD. E. Ward, Y. Gai, Q. Qiao, J. Shen, Can. J. Chem. 2004, 82, 254–267.
- 296D. E. Ward, J. Shen, Org. Lett. 2007, 9, 2843–2846.
- 297S. K. Sabui, R. V. Venkateswaran, Tetrahedron Lett. 2004, 45, 983–985.
- 298T. Morimoto, T. Horiguchi, K. Yamada, K. Tsutsumi, H. Kurosawa, K. Kakiuchi, Synthesis 2004, 753–756.
- 299G. Mehta, K. Srinivas, Tetrahedron Lett. 2001, 42, 2855–2857.
- 300
- 300aG. Mehta, K. Sreenivas, Chem. Commun. 2001, 1892–1893;
- 300bG. Mehta, K. Sreenivas, Tetrahedron Lett. 2002, 43, 3319–3321.
- 301T. Bach, A. Spiegel, Synlett 2002, 1305–1307.
- 302J. E. McMurry, W. Choy, Tetrahedron Lett. 1980, 21, 2477–2480.
- 303C. R. Johnson, N. A. Meanwell, J. Am. Chem. Soc. 1981, 103, 7667–7669.
- 304
- 304aM. Fleck, T. Bach, Angew. Chem. 2008, 120, 6284–6286;
10.1002/ange.200801534 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 6189–6191;
- 304bM. Fleck, T. Bach, Chem. Eur. J. 2010, 16, 6015–6032.
- 305I. K. Mangion, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 3696–3697.
- 306A. Srikrishna, S. S. V. Ramasastry, Tetrahedron Lett. 2005, 46, 7373–7376.
- 307T. Fujimori, R. Kasuga, H. Kaneko, S. Sakamura, M. Noguchi, A. Furusaki, N. Hashiba, T. Matsumoto, J. Chem. Soc. Chem. Commun. 1978, 563–564.
- 308J. Leimner, H. Marschall, N. Meier, P. Weyerstahl, Chem. Lett. 1984, 1769–1772.
- 309L. B. Nielsen, D. Wege, Org. Biomol. Chem. 2006, 4, 868–876.
- 310W. G. Dauben, G. Shapiro, J. Org. Chem. 1984, 49, 4252–4258.
- 311
- 311aK. C. Nicolaou, D. Sarlah, D. M. Shaw, Angew. Chem. 2007, 119, 4792–4795;
10.1002/ange.200701552 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 4708–4711;
- 311bK. C. Nicolaou, T. R. Wu, D. Sarlah, D. M. Shaw, E. Rowcliffe, D. R. Burton, J. Am. Chem. Soc. 2008, 130, 11114–11121;
- 311cC. Du, L. Li, Y. Li, Z. Xie, Angew. Chem. 2009, 121, 7993–7996; Angew. Chem. Int. Ed. 2009, 48, 7853–7856.
- 312J. D. White, D. N. Gupta, J. Am. Chem. Soc. 1968, 90, 6171–6177.
- 313
- 313aK. Tomioka, M. Tanaka, K. Koga, Tetrahedron Lett. 1982, 23, 3401–3404;
- 313bK. Tomioka, M. Tanaka, K. Koga, Chem. Pharm. Bull. 1989, 37, 1201–1207.
- 314
- 314aM. Tanaka, K. Tomioka, K. Koga, Tetrahedron Lett. 1985, 26, 3035–3038;
- 314bM. Tanaka, K. Tomioka, K. Koga, Tetrahedron 1994, 50, 12829–12842.
- 315
- 315aM. Tanaka, K. Tomioka, K. Koga, Tetrahedron Lett. 1985, 26, 6109–6112;
- 315bM. Tanaka, K. Tomioka, K. Koga, Tetrahedron 1994, 50, 12843–12852;
- 315cW. G. Dauben, B. A. Kowalczyk, Tetrahedron Lett. 1990, 31, 635–638.
- 316
- 316aR. G. Salomon, N. D. Sachinvala, S. R. Raychaudhuri, D. B. Miller, J. Am. Chem. Soc. 1984, 106, 2211–2213;
- 316bR. G. Salomon, B. Basu, S. Roy, R. B. Sharma, Tetrahedron Lett. 1989, 30, 4621–4624;
- 316cR. G. Salomon, N. D. Sachinvala, S. Roy, B. Basu, S. R. Raychaudhuri, D. B. Miller, R. B. Sharma, J. Am. Chem. Soc. 1991, 113, 3085–3095;
- 316dR. G. Salomon, B. Basu, S. Roy, N. D. Sachinvala, J. Am. Chem. Soc. 1991, 113, 3096–3106.
- 317
- 317aV. Mascitti, E. J. Corey, J. Am. Chem. Soc. 2004, 126, 15664–15665;
- 317bV. Mascitti, E. J. Corey, J. Am. Chem. Soc. 2006, 128, 3118–3119.
- 318E. J. Corey, D. E. Cane, L. Libit, J. Am. Chem. Soc. 1971, 93, 7016–7021.
- 319M. Miyashita, A. Yoshikoshi, J. Am. Chem. Soc. 1974, 96, 1917–1925.
- 320
- 320aM. C. Pirrung, Tetrahedron Lett. 1980, 21, 4577–4578;
- 320bP. Hughes, M. Martin, J. Clardy, Tetrahedron Lett. 1980, 21, 4579–4580;
- 320cP. Hughes, J. Clardy, J. Org. Chem. 1988, 53, 4793–4796.
- 321S. Hatakeyama, M. Kawamura, S. Takano, J. Am. Chem. Soc. 2002, 124, 4081–4082.
- 322G. Guella, F. Pietra, F. Dini, Helv. Chim. Acta 1995, 78, 1747–1754.
- 323Übersichten:
- 323aJ. D. Winkler, C. M. Bowen, F. Liotta, Chem. Rev. 1995, 95, 2003–2020;
- 323bW. Oppolzer, Acc. Chem. Res. 1982, 15, 135–141;
- 323cP. de Mayo, Acc. Chem. Res. 1971, 4, 41–47.
- 324H. Takeshita, A. Mori, S. Nakamura, Bull. Chem. Soc. Jpn. 1984, 57, 3152–3155.
- 325S. W. Baldwin, M. T. Crimmins, J. Am. Chem. Soc. 1982, 104, 1132–1134.
- 326T. Hatsui, J.-J. Wang, S.-y. Ikeda, H. Takeshita, Synlett 1995, 35–37.
- 327T. Hatsui, M. Taga, A. Mori, H. Takeshita, Chem. Lett. 1998, 27, 113–114.
10.1246/cl.1998.113 Google Scholar
- 328J. J. Partridge, N. K. Chadha, M. R. Uskokovic, J. Am. Chem. Soc. 1973, 95, 532–540.
- 329
- 329aG. Büchi, J. A. Carlson, J. E. Powell, L. F. Tietze, J. Am. Chem. Soc. 1970, 92, 2165–2167;
- 329bG. Büchi, J. A. Carlson, J. E. Powell, Jr., L. F. Tietze, J. Am. Chem. Soc. 1973, 95, 540–545.
- 330
- 330aL. F. Tietze, Angew. Chem. 1973, 85, 763–765; Angew. Chem. Int. Ed. Engl. 1973, 12, 757–758;
- 330bL. F. Tietze, J. Am. Chem. Soc. 1974, 96, 946–947.
- 331M. Demuth, A. Palomer, H.-D. Sluma, A. K. Dey, C. Krüger, Y.-H. Tsay, Angew. Chem. 1986, 98, 1093–1095; Angew. Chem. Int. Ed. Engl. 1986, 25, 1117–1119.
- 332S. W. Baldwin, G. F. Martin, Jr., D. S. Nunn, J. Org. Chem. 1985, 50, 5720–5723.
- 333H. Takeshita, Y.-S. Cui, N. Kato, A. Mori, Bull. Chem. Soc. Jpn. 1993, 66, 2694–2699.
- 334S. W. Baldwin, J. E. Fredericks, Tetrahedron Lett. 1982, 23, 1235–1238.
- 335S. W. Baldwin, N. G. Landmesser, Tetrahedron Lett. 1982, 23, 4443–4446.
- 336Y. Inouye, M. Shirai, T. Michino, H. Kakisawa, Bull. Chem. Soc. Jpn. 1993, 66, 324–326.
- 337
- 337aG. L. Lange, P. de Mayo, J. Chem. Soc. Chem. Commun. 1967, 704;
- 337bB. D. Challand, H. Hikino, G. Kornis, G. Lange, P. de Mayo, J. Org. Chem. 1969, 34, 794–806.
- 338M. Cavazza, A. Guerriero, F. Pietra, J. Chem. Soc. Perkin Trans. 1 1986, 2005–2008.
- 339B. D. Challand, G. Kornis, G. L. Lange, P. De Mayo, J. Chem. Soc. Chem. Commun. 1967, 704–705.
- 340T. Hansson, B. Wickberg, J. Org. Chem. 1992, 57, 5370–5376.
- 341G. L. Lange, A. Merica, M. Chimanikire, Tetrahedron Lett. 1997, 38, 6371–6374.
- 342G. L. Lange, C. Gottardo, A. Merica, J. Org. Chem. 1999, 64, 6738–6744.
- 343G. L. Lange, C. Gottardo, J. Org. Chem. 1995, 60, 2183–2187.
- 344R. L. Cargill, T. E. Jackson, N. P. Peet, D. M. Pond, Acc. Chem. Res. 1974, 7, 106–113.
- 345D. K. Manh Duc, M. Fetizon, S. Lazare, Tetrahedron 1978, 34, 1207–1212.
10.1016/0040-4020(78)80147-1 Google Scholar
- 346J. D. White, Synthesis 1998, 619–626.
- 347
- 347aK. J. Moriarty, C.-C. Shen, L. A. Paquette, Synlett 1990, 263–264;
- 347bL. A. Paquette, K. J. Moriarty, C.-C. Shen, Isr. J. Chem. 1991, 31, 195–198.
- 348A. Nath, A. Ghosh, R. V. Venkateswaran, J. Org. Chem. 1992, 57, 1467–1472.
- 349Y. Kitano, J. Fukuda, K. Chiba, M. Tada, J. Chem. Soc. Perkin Trans. 1 1996, 829–835.
- 350K. Kakiuchi, M. Ue, H. Tsukahara, T. Shimizu, T. Miyao, Y. Tobe, Y. Odaira, M. Yasuda, K. Shima, J. Am. Chem. Soc. 1989, 111, 3707–3712.
- 351M. Ue, Y. Ohnishi, K. Kobiro, K. Kakiuchi, Y. Tobe, Y. Odaira, Chem. Lett. 1990, 19, 149–150.
- 352M. Yamashita, T. Inaba, T. Shimizu, I. Kawasaki, S. Ohta, Synlett 2004, 1897–1900.
- 353M. Yamashita, N. D. Yadav, T. Sawaki, I. Takao, I. Kawasaki, Y. Sugimoto, A. Miyatake, K. Murai, A. Takahara, A. Kurume, S. Ohta, J. Org. Chem. 2007, 72, 5697–5703.
- 354K. Yamakawa, R. Sakaguchi, T. Nakamura, K. Watanabe, Chem. Lett. 1976, 991–992.
- 355T. Naito, C. Kaneko, Chem. Pharm. Bull. 1983, 31, 366–369.
- 356G. L. Lange, L. Furlan, M. C. MacKinnon, Tetrahedron Lett. 1998, 39, 5489–5492.
- 357
- 357aH.-J. Liu, M. Llinas-Brunet, Can. J. Chem. 1988, 66, 528–530;
- 357bsiehe auch: P. Magnus, L. M. Principe, M. J. Slater, J. Org. Chem. 1987, 52, 1483–1486.
- 358H. Nagaoka, M. Shimano, Y. Yamada, Tetrahedron Lett. 1989, 30, 971–974.
- 359H. Koyama, H. Okawara, S. Kobayashi, M. Ohno, Tetrahedron Lett. 1985, 26, 2685–2688.
- 360C. Iwata, Y. Takemoto, M. Doi, T. Imanishi, J. Org. Chem. 1988, 53, 1623–1628.
- 361S. L. Schreiber, C. Santini, J. Am. Chem. Soc. 1984, 106, 4038–4039.
- 362
- 362aA. B. Smith III, R. E. Richmond, J. Org. Chem. 1981, 46, 4814–4816;
- 362bA. B. Smith III, R. E. Richmond, J. Am. Chem. Soc. 1983, 105, 575–585.
- 363H. J. Liu, M. G. Kulkarni, Tetrahedron Lett. 1985, 26, 4847–4850.
- 364H. J. Liu, W. H. Chan, Can. J. Chem. 1982, 60, 1081–1091.
- 365
- 365aP. Selig, T. Bach, Angew. Chem. 2008, 120, 5160–5162;
10.1002/ange.200800693 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 5082–5084;
- 365bP. Selig, E. Herdtweck, T. Bach, Chem. Eur. J. 2009, 15, 3509–3525.
- 366
- 366aT. Bach, H. Bergmann, K. Harms, Angew. Chem. 2000, 112, 2391–2393;
Angew. Chem. Int. Ed. 2000, 39, 2302–2304;
10.1002/1521-3773(20000703)39:13<2302::AID-ANIE2302>3.0.CO;2-6 CAS PubMed Web of Science® Google Scholar
- 366bT. Bach, H. Bergmann, J. Am. Chem. Soc. 2000, 122, 11525–11526;
- 366cT. Bach, H. Bergmann, B. Grosch, K. Harms, E. Herdtweck, Synthesis 2001, 1395–1405.
- 367T. Sano, J. Toda, T. Ohshima, Y. Tsuda, Chem. Pharm. Bull. 1992, 40, 873–878.
- 368Y. Tsuda, T. Ohshima, S. Hosoi, S. Kaneuchi, F. Kiuchi, J. Toda, T. Sano, Chem. Pharm. Bull. 1996, 44, 500–508.
- 369A. B. Smith III, P. J. Jerris, J. Am. Chem. Soc. 1981, 103, 194–195.
- 370K. Takeda, Y. Shimono, E. Yoshii, J. Am. Chem. Soc. 1983, 105, 563–568.
- 371A. B. Smith III, J. P. Konopelski, J. Org. Chem. 1984, 49, 4094–4095.
- 372A. Abad, C. Agulló, M. Arnó, M. L. Marín, R. J. Zaragozá, J. Chem. Soc. Perkin Trans. 1 1994, 2987–2991.
- 373A. Abad, M. Arnó, A. C. Cunat, M. L. Marín, R. J. Zaragozá, J. Org. Chem. 1992, 57, 6861–6869.
- 374R. M. Scarborough, Jr., A. B. Smith III, J. Am. Chem. Soc. 1977, 99, 7085–7087.
- 375D. Boschelli, A. B. Smith III, Tetrahedron Lett. 1981, 22, 3733–3736.
- 376G. Mehta, S. R. Singh, Angew. Chem. 2006, 118, 967–969; Angew. Chem. Int. Ed. 2006, 45, 953–956.
- 377M. Inoue, T. Sato, M. Hirama, Angew. Chem. 2006, 118, 4961–4966; Angew. Chem. Int. Ed. 2006, 45, 4843–4848.
- 378H. Nagaoka, H. Miyaoka, Y. Yamada, Tetrahedron Lett. 1990, 31, 1573–1576.
- 379R. A. Whitney, Can. J. Chem. 1983, 61, 1158–1160.
- 380
- 380aA. B. Smith III, G. A. Sulikowski, K. Fujimoto, J. Am. Chem. Soc. 1989, 111, 8039–8041;
- 380bA. B. Smith III, G. A. Sulikowski, M. M. Sulikowski, K. Fujimoto, J. Am. Chem. Soc. 1992, 114, 2567–2576.
- 381H.-J. Liu, S. P. Lee, Tetrahedron Lett. 1977, 18, 3699–3702.
10.1016/S0040-4039(01)83330-X Google Scholar
- 382H. Suginome, Y. Nakayama, Tetrahedron 1994, 50, 7771–7782.
- 383K. Tatsuta, K. Akimoto, M. Kinoshita, J. Am. Chem. Soc. 1979, 101, 6116–6118.
- 384K. Tatsuta, K. Akimoto, M. Kinoshita, Tetrahedron 1981, 37, 4365–4369.
- 385Y. Tobe, T. Yamashita, K. Kakiuchi, Y. Odaira, J. Chem. Soc. Chem. Commun. 1985, 898–899.
- 386Y. Tobe, S. Yamashita, T. Yamashita, K. Kakiuchi, Y. Odaira, J. Chem. Soc. Chem. Commun. 1984, 1259–1260.
- 387L. Van Hijfte, M. Vandewalle, Tetrahedron Lett. 1982, 23, 2229–2232.
- 388L. Van Hijfte, M. Vandewalle, Tetrahedron 1984, 40, 4371–4382.
- 389T. A. Anglea, A. R. Pinder, Tetrahedron 1987, 43, 5537–5543.
- 390D. Termont, P. De Clercq, D. D. Keukeleire, M. Vandewalle, Synthesis 1977, 46–48.
- 391P. De Clercq, M. Vandewalle, J. Org. Chem. 1977, 42, 3447–3450.
- 392P. Kok, P. De Clercq, M. Vandewalle, Bull. Soc. Chim. Belg. 1978, 87, 615–619.
- 393P. Kok, P. J. De Clercq, M. E. Vandewalle, J. Org. Chem. 1979, 44, 4553–4557.
- 394M. Demuynck, P. De Clercq, M. Vandewalle, J. Org. Chem. 1979, 44, 4863–4866.
- 395A. A. Devreese, P. J. De Clercq, M. Vandewalle, Tetrahedron Lett. 1980, 21, 4767–4770.
- 396A. A. Devreese, M. Demuynck, P. J. De Clercq, M. Vandewalle, Tetrahedron 1983, 39, 3049–3054.
- 397M. Demuynck, A. A. Devreese, P. J. De Clercq, M. Vandewalle, Tetrahedron Lett. 1982, 23, 2501–2504.
- 398G. L. Lange, A. Merica, Tetrahedron Lett. 1998, 39, 3639–3642.
- 399P. A. Wender, J. C. Lechleiter, J. Am. Chem. Soc. 1980, 102, 6340–6341.
- 400P. A. Wender, J. C. Hubbs, J. Org. Chem. 1980, 45, 365–367.
- 401P. A. Wender, L. J. Letendre, J. Org. Chem. 1980, 45, 367–368.
- 402J. R. Williams, J. F. Callahan, J. Org. Chem. 1980, 45, 4479–4483.
- 403P. A. Wender, S. L. Eck, Tetrahedron Lett. 1982, 23, 1871–1874.
- 404J. R. Williams, J. F. Callahan, C. Lin, J. Org. Chem. 1983, 48, 3162–3163.
- 405F. Audenaert, D. De Keukeleire, M. Vandewalle, Tetrahedron 1987, 43, 5593–5604.
- 406
- 406aJ. R. Williams, J. F. Callahan, J. Chem. Soc. Chem. Commun. 1979, 404–405;
- 406bJ. R. Williams, J. F. Callahan, J. Org. Chem. 1980, 45, 4475–4478.
- 407J. R. Williams, C. Lin, D. F. Chodosh, J. Org. Chem. 1985, 50, 5815–5822.
- 408
- 408aR. Srinivasan, K. H. Carlough, J. Am. Chem. Soc. 1967, 89, 4932–4936;
- 408bR. S. H. Liu, G. S. Hammond, J. Am. Chem. Soc. 1967, 89, 4936–4944;
- 408cD. J. Maradyn, A. C. Weedon, J. Am. Chem. Soc. 1995, 117, 5359–5360.
- 409
- 409aW. Oppolzer, T. Godel, J. Am. Chem. Soc. 1978, 100, 2583–2584;
- 409bW. Oppolzer, T. Godel, Helv. Chim. Acta 1984, 67, 1154–1167.
- 410H. Seto, Y. Fujimoto, T. Tatsuno, H. Yoshioka, Synth. Commun. 1985, 15, 1217–1224.
- 411W. Oppolzer, R. D. Wylie, Helv. Chim. Acta 1980, 63, 1198–1203.
- 412
- 412aG. Pattenden, G. M. Robertson, Tetrahedron Lett. 1986, 27, 399–402;
- 412bM. J. Begley, G. Pattenden, G. M. Robertson, J. Chem. Soc. Perkin Trans. 1 1988, 1085–1094.
- 413J. D. Winkler, M. B. Rouse, M. F. Greaney, S. J. Harrison, Y. T. Jeon, J. Am. Chem. Soc. 2002, 124, 9726–9728.
- 414J. D. Winkler, E. M. Doherty, J. Am. Chem. Soc. 1999, 121, 7425–7426.
- 415J. D. Winkler, P. M. Hershberger, J. Am. Chem. Soc. 1989, 111, 4852–4856.
- 416B. A. Pearlman, J. Am. Chem. Soc. 1979, 101, 6404–6408.
- 417
- 417aA. J. Barker, G. Pattenden, Tetrahedron Lett. 1981, 22, 2599–2600;
- 417bA. J. Barker, G. Pattenden, J. Chem. Soc. Perkin Trans. 1 1983, 1901–1904.
- 418J. D. Winkler, J. M. Axten, J. Am. Chem. Soc. 1998, 120, 6425–6426.
- 419J. D. Winkler, C. L. Muller, R. D. Scott, J. Am. Chem. Soc. 1988, 110, 4831–4832.
- 420J. D. Winkler, R. D. Scott, P. G. Williard, J. Am. Chem. Soc. 1990, 112, 8971–8975.
- 421J. D. White, Y. Li, D. C. Ihle, J. Org. Chem. 2010, 75, 3569–3577.
- 422N. Haddad, H. Salman, Tetrahedron Lett. 1997, 38, 6087–6090.
- 423A. M. Birch, G. Pattenden, J. Chem. Soc. Perkin Trans. 1 1983, 1913–1917.
- 424
- 424aG. Pattenden, S. J. Teague, Tetrahedron Lett. 1984, 25, 3021–3024;
- 424bG. Pattenden, S. J. Teague, Tetrahedron 1987, 43, 5637–5652.
- 425
- 425aM. C. Pirrung, J. Am. Chem. Soc. 1979, 101, 7130–7131;
- 425bM. C. Pirrung, J. Am. Chem. Soc. 1981, 103, 82–87.
- 426
- 426aM. T. Crimmins, J. A. DeLoach, J. Org. Chem. 1984, 49, 2076–2077;
- 426bM. T. Crimmins, J. A. DeLoach, J. Am. Chem. Soc. 1986, 108, 800–806.
- 427M. T. Crimmins, L. D. Gould, J. Am. Chem. Soc. 1987, 109, 6199–6200.
- 428M. T. Crimmins, S. W. Mascarella, J. Am. Chem. Soc. 1986, 108, 3435–3438.
- 429M. T. Crimmins, S. W. Mascarella, Tetrahedron Lett. 1987, 28, 5063–5066.
- 430W. Oppolzer, F. Zutterman, K. Bättig, Helv. Chim. Acta 1983, 66, 522–533.
- 431D. L. Comins, Y.-m. Zhang, X. Zheng, Chem. Commun. 1998, 2509–2510.
- 432M. Ichikawa, S. Aoyagi, C. Kibayashi, Tetrahedron Lett. 2005, 46, 2327–2329.
- 433
- 433aM. T. Crimmins, D. K. Jung, J. L. Gray, J. Am. Chem. Soc. 1992, 114, 5445–5447;
- 433bM. T. Crimmins, D. K. Jung, J. L. Gray, J. Am. Chem. Soc. 1993, 115, 3146–3155.
- 434
- 434aM. T. Crimmins, J. M. Pace, P. G. Nantermet, A. S. Kim-Meade, J. B. Thomas, S. H. Watterson, A. S. Wagman, J. Am. Chem. Soc. 1999, 121, 10249–10250;
- 434bM. T. Crimmins, J. M. Pace, P. G. Nantermet, A. S. Kim-Meade, J. B. Thomas, S. H. Watterson, A. S. Wagman, J. Am. Chem. Soc. 2000, 122, 8453–8463.
- 435
- 435aE. R. Koft, A. B. Smith III, J. Am. Chem. Soc. 1982, 104, 5568–5570;
- 435bE. R. Koft, A. B. Smith III, J. Am. Chem. Soc. 1984, 106, 2115–2121.
- 436M. C. Pirrung, S. A. Thomson, J. Org. Chem. 1988, 53, 227–230.
- 437
- 437aM. T. Crimmins, Z. Wang, L. A. McKerlie, Tetrahedron Lett. 1996, 37, 8703–8706;
- 437bM. T. Crimmins, Z. Wang, L. A. McKerlie, J. Am. Chem. Soc. 1998, 120, 1747–1756.
- 438J. D. White, M. P. Dillon, R. J. Butlin, J. Am. Chem. Soc. 1992, 114, 9673–9674.
- 439G. Mehta, A. V. Reddy, J. Chem. Soc. Chem. Commun. 1981, 756–757.
- 440G. Mehta, A. N. Murthy, D. S. Reddy, A. V. Reddy, J. Am. Chem. Soc. 1986, 108, 3443–3452.
- 441G. Mehta, D. S. Reddy, A. N. Murty, J. Chem. Soc. Chem. Commun. 1983, 824–825.
- 442G. Mehta, J. D. Umarye, Tetrahedron Lett. 2001, 42, 1991–1993.
- 443W. D. Shipe, E. J. Sorensen, J. Am. Chem. Soc. 2006, 128, 7025–7035.
- 444D. Patra, S. Ghosh, J. Chem. Soc. Perkin Trans. 1 1995, 2635–2641.
- 445S. Samajdar, D. Patra, S. Ghosh, Tetrahedron 1998, 54, 1789–1800.
- 446S. Samajdar, A. Ghatak, S. Ghosh, Tetrahedron Lett. 1999, 40, 4401–4402.
- 447
- 447aK. S. Feldman, J. H. Come, A. J. Freyer, B. J. Kosmider, C. M. Smith, J. Am. Chem. Soc. 1986, 108, 1327–1328;
- 447bK. S. Feldman, J. H. Come, B. J. Kosmider, P. M. Smith, D. P. Rotella, M. J. Wu, J. Org. Chem. 1989, 54, 592–601.
- 448B. Gerard, G. Jones, J. A. Porco, Jr., J. Am. Chem. Soc. 2004, 126, 13620–13621.
- 449B. Gerard, S. Sangji, D. J. O’Leary, J. A. Porco, Jr., J. Am. Chem. Soc. 2006, 128, 7754–7755.
- 450
- 450aB. Gerard, R. Cencic, J. Pelletier, J. A. Porco, Jr., Angew. Chem. 2007, 119, 7977–7980;
10.1002/ange.200702707 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 7831–7834;
- 450bT. E. Adams, M. El Sous, B. C. Hawkins, S. Hirner, G. Holloway, M. L. Khoo, D. J. Owen, G. P. Savage, P. J. Scammells, M. A. Rizzacasa, J. Am. Chem. Soc. 2009, 131, 1607–1616.
- 451
- 451aP. Garner, W. B. Ho, H. Shin, J. Am. Chem. Soc. 1992, 114, 2767–2768;
- 451bP. Garner, W. B. Ho, H. Shin, J. Am. Chem. Soc. 1993, 115, 10742–10753.
- 452M. D. Lainchbury, M. I. Medley, P. M. Taylor, P. Hirst, W. Dohle, K. I. Booker-Milburn, J. Org. Chem. 2008, 73, 6497–6505.
- 453B. D. A. Hook, W. Dohle, P. R. Hirst, M. Pickworth, M. B. Berry, K. I. Booker-Milburn, J. Org. Chem. 2005, 70, 7558–7564.
- 454
- 454aK. S. Feldman, M. J. Wu, D. P. Rotella, J. Am. Chem. Soc. 1989, 111, 6457–6458;
- 454bK. S. Feldman, M. J. Wu, D. P. Rotella, J. Am. Chem. Soc. 1990, 112, 8490–8496.
- 455Übersichten:
- 455aU. Streit, C. Bochet, Chimia 2008, 62, 962–966;
- 455bJ. Mattay, Angew. Chem. 2007, 119, 674–677;
10.1002/ange.200603337 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 663–665;
- 455cD. Chappell, A. T. Russell, Org. Biomol. Chem. 2006, 4, 4409–4430;
- 455dN. Hoffmann in Molecular and Supramolecular Photochemistry, Vol. 12 (Hrsg.: ), Marcel Dekker, New York, 2005, S. 529–552;
- 455eA. Gilbert in CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. ), CRC, Boca Raton, 2004, S. 41/1–41/11;
- 455fN. Hoffmann, Synthesis 2004, 481–495;
- 455gJ. Cornelisse, Chem. Rev. 1993, 93, 615–669;
- 455hD. De Keukeleire, S.-L. He, Chem. Rev. 1993, 93, 359–380;
- 455iJ. Mattay, J. Photochem. 1987, 37, 167–183.
- 456
- 456aP. A. Wender, T. M. Dore in CRC Handbook of Organic Photochemistry and Photobiology (Hrsg.: ), CRC, Boca Raton, 1995, S. 280–290;
- 456bP. A. Wender, L. Siggel, J. M. Nuss in Comprehensive Organic Synthesis, Vol. 5 (Hrsg.: ), Pergamon, Oxford, 1991, S. 645–673;
10.1016/B978-0-08-052349-1.00135-9 Google Scholar
- 456cP. A. Wender, R. Ternansky, M. deLong, S. Singh, A. Olivero, K. Rice, Pure Appl. Chem. 1990, 62, 1597–1602;
- 456dP. A. Wender, L. Siggel, J. M. Nuss, Org. Photochem. 1989, 10, 357–473;
- 456eP. A. Wender in Selectivity – a Goal for Synthetic Efficiency (Hrsg.: ), Verlag Chemie, Weinheim, 1984, S. 335–348.
- 457P. A. Wender, G. B. Dreyer, J. Am. Chem. Soc. 1982, 104, 5805–5807.
- 458P. A. Wender, G. B. Dreyer, Tetrahedron Lett. 1983, 24, 4543–4546.
- 459R. W. Hoffmann, Chem. Rev. 1989, 89, 1841–1860.
- 460P. A. Wender, K. Fisher, Tetrahedron Lett. 1986, 27, 1857–1860.
- 461P. A. Wender, J. J. Howbert, Tetrahedron Lett. 1982, 23, 3983–3986.
- 462P. A. Wender, J. J. Howbert, Tetrahedron Lett. 1983, 24, 5325–5328.
- 463C. Baralotto, M. Chanon, M. Julliard, J. Org. Chem. 1996, 61, 3576–3577.
- 464P. A. Wender, T. W. Von Geldern, B. H. Levine, J. Am. Chem. Soc. 1988, 110, 4858–4860.
- 465T. Gaich, J. Mulzer, J. Am. Chem. Soc. 2009, 131, 452–453.
- 466T. Gaich, J. Mulzer, Org. Lett. 2010, 12, 272–275.
- 467P. A. Wender, G. B. Dreyer, Tetrahedron 1981, 37, 4445–4450.
- 468P. A. Wender, R. J. Ternansky, Tetrahedron Lett. 1985, 26, 2625–2628.
- 469P. A. Wender, S. K. Singh, Tetrahedron Lett. 1985, 26, 5987–5990.
- 470P. A. Wender, S. K. Singh, Tetrahedron Lett. 1990, 31, 2517–2520.
- 471P. A. Wender, M. A. deLong, Tetrahedron Lett. 1990, 31, 5429–5432.
- 472P. A. Wender, T. M. Dore, Tetrahedron Lett. 1998, 39, 8589–8592.
- 473Übersichten:
- 473aC. Müller, T. Bach, Aust. J. Chem. 2008, 61, 557–564;
- 473bP. Wessig, Angew. Chem. 2006, 118, 2224–2227;
10.1002/ange.200503908 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 2168–2171;
- 473cT. Bach, B. Grosch in CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. ), CRC, Boca Raton, 2004, S. 61/1–61/14;
- 473dB. Grosch, T. Bach in Molecular and Supramolecular Photochemistry, Vol. 11 (Hrsg.: ), Marcel Dekker, New York, 2004, S. 315–340.
- 474
- 474aA. Bauer, F. Westkämper, S. Grimme, T. Bach, Nature 2005, 436, 1139–1140;
- 474bC. Müller, A. Bauer, T. Bach, Angew. Chem. 2009, 121, 6767–6769; Angew. Chem. Int. Ed. 2009, 48, 6640–6642.
- 475Keine andere Totalsynthese veranschaulicht diesen Satz vermutlich besser als die legendäre Synthese des Vitamins B12 durch Eschenmoser et al. In einer neuartigen, photochemischen Cycloisomerisierung gelang der Aufbau des Corringerüsts ausgehend von einem seco-corrinoiden Cadmiumkomplex:
- 475aY. Yamada, D. Miljkovic, P. Wehrli, B. Golding, P. Löllinger, R. Keese, K. Müller, A. Eschenmoser, Angew. Chem. 1969, 81, 301–306; Angew. Chem. Int. Ed. 1969, 8, 343–348;
- 475bA. Eschenmoser, C. E. Wintner, Science 1977, 196, 1410–1420.
- 476Beispiele:
- 476aI. Braun, F. Rudroff, M. D. Mihovilovic, T. Bach, Angew. Chem. 2006, 118, 5667–5670; Angew. Chem. Int. Ed. 2006, 45, 5541–5543;
- 476bS. R. Schulz, S. Blechert, Angew. Chem. 2007, 119, 4040–4044;
10.1002/ange.200604553 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 3966–3970;
- 476cF. Frébault, M. Luparia, M. T. Oliveira, R. Goddard, N. Maulide, Angew. Chem. 2010, 5807–5811; Angew. Chem. Int. Ed. 2010, 49, 5672–5676.
- 477Beispiel: M. A. Ischay, M. E. Anzovino, J. Du, T. P. Yoon, J. Am. Chem. Soc. 2008, 130, 12886–12887.
- 478Nach Abschluss der Arbeiten zu diesem Aufsatz sind weitere Naturstoffsynthesen erschienen, die wir mit thematischem Verweis auf den jeweilige Abschnitt chronologisch auflisten:
- 478a(+)-Deoxypseudopterolid: Z. Yang, Y. Li, G. Pattenden, Tetrahedron 2010, 66, 6546–6549 (Abschnitt 5);
- 478b(+)-Connatusin B: D. J.-Y. D. Bon, M. G. Banwell, A. C. Willis, Tetrahedron 2010, 66, 7807–7814 (Abschnitt 5);
- 478c(±)-Biyouyanagin B: K. C. Nicolaou, S. Sanchini, T. R. Wu, D. Sarlah, Chem. Eur. J. 2010, 16, 7678–7682 (Abschnitt 8).
Citing Literature
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.
