Samariumdiiodid-vermittelte Kupplung von Glycosylphosphaten mit Kohlenstoffradikal- oder -anion-Acceptoren – Synthese von C-Glycosiden†
Dr. Shang-Cheng Hung
Department of Chemistry, The Scripps Research Institute 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA) Telefax: Int. + 619/784–2409
Search for more papers by this authorCorresponding Author
Prof. Dr. Chi-Huey Wong
Department of Chemistry, The Scripps Research Institute 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA) Telefax: Int. + 619/784–2409
Department of Chemistry, The Scripps Research Institute 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA) Telefax: Int. + 619/784–2409Search for more papers by this authorDr. Shang-Cheng Hung
Department of Chemistry, The Scripps Research Institute 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA) Telefax: Int. + 619/784–2409
Search for more papers by this authorCorresponding Author
Prof. Dr. Chi-Huey Wong
Department of Chemistry, The Scripps Research Institute 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA) Telefax: Int. + 619/784–2409
Department of Chemistry, The Scripps Research Institute 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA) Telefax: Int. + 619/784–2409Search for more papers by this authorWir danken Dr. Kap-Sun Yeung und Chung-Cheng Lin für einige Ausgangsverbindungen.
Abstract
Die als Kohlenhydratmimetica bei Erkennungsprozessen in biologischen Systemen eingesetzten C-Glycoside lassen sich durch SmI2-vermittelte Kupplung von Glycosylphosphaten mit Kohlenstoffradikal-oder Kohlenstoffanionen-Acceptoren synthetisieren. Die Reaktion verläuft wahrscheinlich in Einelektronen-schritten über Radikale oder Anionen als Zwischen-stufe (siehe rechts).
References
- 1a) A. Wei, K. M. Boy, Y. Kishi, J. Am. Chem. Soc. 1995, 117, 9432; b) A. Wei, A. Haudrechy, C. Audin, H.-S. Jun, N. Haudrechy-Bretel, Y. Kishi, J. Org. Chem. 1995, 60, 2160; c) D. J. O'Leary, Y. Kishi, J. Org. Chem. 1994, 59, 6629; d) A. Wei, Y. Kishi, J. Org. Chem. 1994, 59, 88; e) D. J. O'Leary, Y. Kishi, J. Org. Chem. 1993, 58, 304; f) J.-F. Espinosa, M. Martin-Pastor, J. L. Asensio, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jimenez-Barbero, Tetrahedron Lett. 1995, 36, 6329.
- 2 C. Barbaud, M. Bols, I. Lundt, M. R. Sierks, Tetrahedron 1995, 51, 9063.
- 3a) W. Spevak, J. O. Nagy, D. H. Charych, M. E. Schaefer, J. H. Gilbert, M. D. Bednarski, J. Am. Chem. Soc. 1993, 115, 1146; b) J. O. Naggy, P. Wang, J. H. Gilbert, M. E. Schaefer, T. G. Hill, M. R. Callstrom, M. D. Bednarski, J. Med. Chem. 1992, 35, 4501; c) C. R. Bertozzi, D. G. Cook, W. R. Kobertz, F. Gonzalez-Scarano, M. D. Bednarski, J. Am. Chem. Soc. 1992, 114, 10 639; d) C. R. Bertozzi, M. D. Bednarski, J. Am. Chem. Soc. 1992, 114, 5543; e) C. R. Bertozzi, P. D. Hoeprich, M. D. Bednarski, J. Org. Chem. 1992, 57, 6092; f) C. R. Bertozzi, M. D. Bednarski, Carbohydr. Res. 1992, 223, 243.
- 4a) H. Kessler, V. Wittmann, M. Kock, M. Kottenhahn, Angew. Chem. 1992, 104, 874; Angew. Chem. Int. Ed. Engl. 1992, 31, 902; b) R. R. Schmidt, H. Dietrich, Angew. Chem. Int. Ed. Engl. 1991, 103, 1348 bzw. Angew. Chem. Int. Ed. Engl. 1991, 30, 1328; c) J. N. BeMiller, M. P. Yadar, V. N. Kalabokis, R. W. Myers, Carbohydr. Res. 1990, 200, 111.
- 5a) X. Wang, P. H. Gross, J. Org. Chem. 1995, 60, 1201; b) J. M. Tronchet, M. Balkadjian, G. Zosimo-Landolfo, F. Barbalat-Rey, P. Lichtle, A. Ricca, I. Komaromi, G. Bernardinelli, M. Geoffroy, J. Carbohydr. Chem. 1995, 14, 17.
- 6a) K. J. Kaur, O. Hindsgaul, Carbohydr. Res. 1992, 226, 219; b) K. N. Drew, P. H. Gross, Tetrahedron 1991, 47, 6113.
- 7a) U. Hacksell, G. D. Daves, Jr., Prog. Med. Chem. 1985, 22, 1; b) K. M. Valant-Vetschera, Bot. Rev. 1985, 51, 1; c) P. Tan, C.-Y. Hou, Y.-L. Liu, L.-J. Lin, G.-A. Cordell, J. Org. Chem. 1991, 56, 7130.
- 8a) M. H. D. Postema, C-Glycoside Synthesis, CRC Press, 1995; b) P. C. Tang, D. E. Levy, Chemistry of C-Glycosides, Elsevier, 1995; c) G. Casiraghi, F. Zanardi, G. Rassu, P. Spanu, Chem. Rev. 1995, 95, 1677; d) C. Jaramillo, S. Knapp, Synthesis 1994, 1; e) M. H. D. Postema, Tetrahedron 1992, 48, 8545; f) J. Herscovici, K. Antonakis, Studies in Natural Products Chemistry, Vol. 10 (Hrsg.: Atta-ur-Rahman), Elsevier, Amsterdam, 1992, S. 337.
- 9a) P. D. Pouilly, A. Chenede, J.-M. Mallet, P. Sinaÿ, Bull. Soc. Chim. Fr. 1993, 130, 256; b) Tetrahedron Lett. 1992, 33, 8065; c) P. D. Pouilly, B. Vauzeilles, J.-M. Mallet, P. Sinaÿ, C. R. Acad. Sci. Ser. 2 1991, 313, 1391; d) P. Sinaÿ, Phosphorus Sulfur Silicon Relat. Elem. 1994, 95–96, 89.
- 10a)
D. Mazeas,
T. Skrydstrup,
J.-M. Beau,
Angew. Chem.
1995,
107,
990;
10.1002/ange.19951070818 Google ScholarAngew. Chem. Int. Ed. Engl. 1995, 34, 909; b) D. Mazeas, T. Skrydstrup, O. Doumeix, J.-M. Beau, Angew. Chem. Int. Ed. Engl. 1994, 106, 1457 bzw. Angew. Chem. Int. Ed. Engl. 1994, 33, 1383.
- 11a) O. Frey, M. Hoffmann, H. Kessler, Angew. Chem. 1995, 107, 2194; Angew. Chem. Int. Ed. Engl. 1995, 34, 2026; b) O. Frey, M. Hoffmann, V. Wittmann, H. Kessler, Helv. Chim. Acta 1994, 77, 2060; c) V. Wittmann, H. Kessler, Angew. Chem. 1993, 105, 1138; Angew. Chem. Int. Ed. Engl. 1993, 32, 1091.
- 12 R. Yoneda, S. Harusawa, T. Kurihara, Tetrahedron Lett. 1989, 30, 3681.
- 13 S. Araki, M. Hatano, H. Ito, Y. Butsugan, J. Organomet. Chem. 1987, 333, 329.
- 14a) H. Kondo, Y. Ichikawa, C.-H. Wong, J. Am. Chem. Soc. 1992, 114, 8748; b) M. M. Sim, H. Kondo, C.-H. Wong, J. Am. Chem. Soc. 1993, 115, 2260; c) H. Kondo, S. Aoki, Y. Ichikawa, R. L. Halcomb, H. Ritzen, C.-H. Wong, J. Org. Chem. 1994, 59, 864.
- 15 S.-I. Hashimoto, T. Honda, S. Ikegami, J. Chem. Soc. Chem. Commun. 1989, 685.
- 16 D. L. Boger, T. Honda, J. Am. Chem. Soc. 1994, 116, 5647.
- 17
Übersichtsartikel: a)
G. A. Molander,
C. R. Harris,
Chem. Rev.
1996,
96,
307;
b)
T. Imamoto,
Lanthanides in Organic Synthesis,
Academic Press,
1994;
c)
G. A. Molander
in
Organic Reactions,
Vol. 46
(Hrsg.: L. A. Paquette),
John Wiley,
1994,
S. 211;
10.1002/0471264180.or046.03 Google Scholard) D. P. Curran, T. L. Fevig, C. P. Jasperse, M. L. Totleben, Synlett 1992, 943; e) J. L. Namy, J. Collin, C. Bied, H. B. Kagan, Synlett 1992, 733; f) G. A. Molander, Chem. Rev. 1992, 92, 29.
- 18 D. Rouzaud, P. Sinaÿ, J. Chem. Soc. Chem. Commun. 1983, 1353.
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