What is Amphidinolide V? Report on a Likely Conquest†
Alois Fürstner Prof.
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim an der Ruhr, Germany, Fax: (+49) 208-306-2994
Search for more papers by this authorOleg Larionov Dr.
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim an der Ruhr, Germany, Fax: (+49) 208-306-2994
Search for more papers by this authorSusanne Flügge Dipl.-Chem.
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim an der Ruhr, Germany, Fax: (+49) 208-306-2994
Search for more papers by this authorAlois Fürstner Prof.
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim an der Ruhr, Germany, Fax: (+49) 208-306-2994
Search for more papers by this authorOleg Larionov Dr.
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim an der Ruhr, Germany, Fax: (+49) 208-306-2994
Search for more papers by this authorSusanne Flügge Dipl.-Chem.
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim an der Ruhr, Germany, Fax: (+49) 208-306-2994
Search for more papers by this authorGenerous financial support from the MPG and the Fonds der Chemischen Industrie (Kekulé fellowship to S.F.) is gratefully acknowledged. We thank Prof. J.-I. Kobayashi for an exchange of information.
Graphical Abstract
Die beeindruckende Leistungsfähigkeit der Metathese zeigt sich in der Synthese der für den cytotoxischen Naturstoff Amphidinolid V vorgeschlagenen Struktur sowie aller anderen Stereomere mit einer trans-Epoxideinheit. Aus dem erhaltenen umfangreichen Datensatz lässt sich folgern, dass die 8S,9R,10R,13S-konfigurierte Verbindung 1 höchstwahrscheinlich Amphidinolid V ist, auch wenn ein 1H-NMR-Signal vom beschriebenen Wert abweicht.
Supporting Information
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References
- 1J. Kobayashi, M. Tsuda, Nat. Prod. Rep. 2004, 21, 77–93.
- 2For the synthesis of various amphidinolides, see Ref. [3] and the following for leading references:
- 2aD. R. Williams, W. S. Kissel, J. Am. Chem. Soc. 1998, 120, 11198–11199;
- 2bD. R. Williams, B. J. Myers, L. Mi, Org. Lett. 2000, 2, 945–948;
- 2cD. R. Williams, K. G. Meyer, J. Am. Chem. Soc. 2001, 123, 765–766;
- 2dH. W. Lam, G. Pattenden, Angew. Chem. 2002, 114, 526–529;
Angew. Chem. Int. Ed. 2002, 41, 508–511;
10.1002/1521-3773(20020201)41:3<508::AID-ANIE508>3.0.CO;2-7 CAS PubMed Web of Science® Google Scholar
- 2eR. E. Maleczka, Jr., L. R. Terrell, F. Geng, J. S. Ward, Org. Lett. 2002, 4, 2841–2844;
- 2fB. M. Trost, P. E. Harrington, J. D. Chisholm, S. T. Wrobleski, J. Am. Chem. Soc. 2005, 127, 13598–13610;
- 2gB. M. Trost, S. T. Wrobelski, J. D. Chisholm, P. E. Harrington, M. Jung, J. Am. Chem. Soc. 2005, 127, 13589–13597;
- 2hP. Va, W. R. Roush, J. Am. Chem. Soc. 2006, 128, 15960–15961;
- 2iC. H. Kim, H. J. An, W. K. Shin, W. Yu, S. K. Woo, S. K. Jung, E. Lee, Angew. Chem. 2006, 118, 8187–8189; Angew. Chem. Int. Ed. 2006, 45, 8019–8021;
- 2jK. C. Nicolaou, W. E. Brenzovich, P. G. Bulger, T. M. Francis, Org. Biomol. Chem. 2006, 4, 2119–2157;
- 2kK. C. Nicolaou, P. G. Bulger, W. E. Brenzovich, Org. Biomol. Chem. 2006, 4, 2158–2183;
- 2lB. M. Trost, J. P. N. Papillon, T. Nussbaumer, J. Am. Chem. Soc. 2005, 127, 17921–17937;
- 2mA. K. Ghosh, G. Gong, J. Org. Chem. 2006, 71, 1085–1093;
- 2nE. A. Colby, K. C. O'Brien, T. F. Jamison, J. Am. Chem. Soc. 2005, 127, 4297–4307;
- 2oE. A. Colby, T. F. Jamison, Org. Biomol. Chem. 2005, 3, 2675–2684;
- 2pL.-S. Deng, X.-P. Huang, G. Zhao, J. Org. Chem. 2006, 71, 4625–4635.
- 3
- 3aA. Fürstner, E. Kattnig, O. Lepage, J. Am. Chem. Soc. 2006, 128, 9194–9204;
- 3bC. Aïssa, R. Riveiros, J. Ragot, A. Fürstner, J. Am. Chem. Soc. 2003, 125, 15512–15520;
- 3cO. Lepage, E. Kattnig, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 15970–15971;
- 3dA. Fürstner, C. Aïssa, R. Riveiros, J. Ragot, Angew. Chem. 2002, 114, 4958–4960;
10.1002/ange.200290041 Google ScholarAngew. Chem. Int. Ed. 2002, 41, 4763–4766.
- 4T. Kubota, M. Tsuda, J. Kobayashi, Tetrahedron Lett. 2000, 41, 713–716.
- 5
- 5aA. Fürstner, C. Nevado, M. Tremblay, C. Chevrier, F. Teplý, C. Aïssa, M. Waser, Angew. Chem. 2006, 118, 5969–5974;
10.1002/ange.200601860 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 5837–5842;
- 5bA. Fürstner, C. Aïssa, C. Chevrier, F. Teplý, C. Nevado, M. Tremblay, Angew. Chem. 2006, 118, 5964–5969;
10.1002/ange.200601859 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 5832–5837;
- 5cA. Fürstner, M. M. Domostoj, B. Scheiper, J. Am. Chem. Soc. 2006, 128, 8087–8094;
- 5dA. Fürstner, L. Turet, Angew. Chem. 2005, 117, 3528–3532;
10.1002/ange.200500390 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 3462–3466;
- 5eA. Fürstner, M. D. B. Fenster, B. Fasching, C. Godbout, K. Radkowski, Angew. Chem. 2006, 118, 5632–5636;
10.1002/ange.200601654 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 5506–5510;
- 5fA. Fürstner, M. D. B. Fenster, B. Fasching, C. Godbout, K. Radkowski, Angew. Chem. 2006, 118, 5636–5641;
10.1002/ange.200601655 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 5510–5515;
- 5gA. Fürstner, D. De Souza, L. Turet, M. D. B. Fenster, L. Parra-Rapado, C. Wirtz, R. Mynott, Chem. Eur. J. 2007, 13, 115–134;
- 5hA. Fürstner, D. Kirk, M. D. B. Fenster, C. Aïssa, D. De Souza, C. Nevado, C. T. T. Tuttle, W. Thiel, O. Müller, Chem. Eur. J. 2007, 13, 135–149, and references therein.
- 6
- 6aA. Fürstner, G. Seidel, Angew. Chem. 1998, 110, 1758–1760;
10.1002/(SICI)1521-3757(19980619)110:12<1758::AID-ANGE1758>3.0.CO;2-I Google ScholarAngew. Chem. Int. Ed. 1998, 37, 1734–1736;10.1002/(SICI)1521-3773(19980703)37:12<1734::AID-ANIE1734>3.0.CO;2-6 CAS PubMed Web of Science® Google Scholar
- 6bA. Fürstner, O. Guth, A. Rumbo, G. Seidel, J. Am. Chem. Soc. 1999, 121, 11108–11113;
- 6cfor a review, see A. Fürstner, P. W. Davies, Chem. Commun. 2005, 2307–2320.
- 7
- 7aK. Tonogaki, M. Mori, Tetrahedron Lett. 2002, 43, 2235–2238;
- 7bM. Mori, Adv. Synth. Catal. 2007, 349, 121–135;
- 7cS. T. Diver, A. J. Giessert, Chem. Rev. 2004, 104, 1317–1382.
- 8For details, see the Supporting Information.
- 9
- 9aG. A. Molander, L. A. Felix, J. Org. Chem. 2005, 70, 3950–3956;
- 9bG. A. Molander, N. Ellis, Acc. Chem. Res. 2007, 40, 275–286.
- 10R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis, 2nd ed. ), Wiley-VCH, New York, 2000, pp. 231–280.
- 11T. Shibata, K. Nakatsui, K. Soai, Inorg. Chim. Acta 1999, 296, 33–36.
- 12
- 12aA. Fürstner, C. Mathes, C. W. Lehmann, J. Am. Chem. Soc. 1999, 121, 9453–9454;
- 12bA. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299–5317;
10.1002/1521-3765(20011217)7:24<5299::AID-CHEM5299>3.0.CO;2-X CAS PubMed Web of Science® Google Scholar
- 12cA. Fürstner, K. Grela, C. Mathes, C. W. Lehmann, J. Am. Chem. Soc. 2000, 122, 11799–11805.
- 13P. R. Blakemore, J. Chem. Soc. Perkin Trans. 1 2002, 2563–2585.
- 14Not considered were isomers with different double-bond geometries as well as isomers containing a cis-epoxide unit. The presence of the latter was ruled out on the basis of the 3JH9,H10 coupling constant of 2.2 Hz reported for natural amphidinolide V, which is characteristic of a trans-epoxide, see Ref. [4]. This assignment was corroborated by the NMR data of the synthetic trans epoxides prepared during this investigation, the corresponding coupling constants of which were invariably about 2 Hz.
- 15M. Taniguchi, H. Fujii, K. Oshima, K. Utimoto, Tetrahedron 1995, 51, 679–686.
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