Stereoselective synthesis of the C31-C40/C43-C52 unit of amphidinol 3

Journal of Organic Chemistry

Volumn 74, Issue 22, 2009, Pages 8810-8813

  Kanemoto, Mitsunori ^a   Murata, Michio ^a   Oishi, Tohru ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC DIHYDROXYLATION; ASYMMETRIC EPOXIDATION; CHEMICAL EQUATIONS; CHEMOSELECTIVE REACTIONS; CONCISE SYNTHESIS; CROSS METATHESIS; CROSS-COUPLED; E-OLEFIN; RING SYSTEMS; STEREOGENIC CENTERS; STEREOSELECTIVE SYNTHESIS; TERMINAL OLEFINS; TETRAHYDROPYRAN;

OLEFINS; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

AMPHIDINOL 3; ANTIFUNGAL AGENT; NATURAL PRODUCT; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

AMPHIDINIUM KLEBSII; ANTIFUNGAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DINOFLAGELLATE; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKENES; MOLECULAR CONFORMATION; PYRANS; STEREOISOMERISM;

EID: 70449640055     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901793f     Document Type: Article

References (46)

1. (a) Shimizu, Y. Chem. Rev. 1993, 93, 1685.
2. (b) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897.
3. (a) Satake, M.; Murata, M.; Yasumoto, T.; Fujita, T.; Naoki, H. J. Am. Chem. Soc. 1991, 113, 9859-9861.
4. (b) Murata, M.; Matsuoka, S.; Matsumori, N.; Paul, G. K.; Tachibana, K. J. Am. Chem. Soc. 1999, 121, 870-871.
5. (a) Paul, G. K.; Matsumori, N.; Konoki, K.; Murata, M.; Tachibana, K. J. Mar. Biotechnol. 1997, 5, 124-128.
6. (b) Houdai, T.; Matsuoka, S.; Matsumori, N.; Murata, M. Biochim. Biophys. Acta 2004, 1667, 91-100.
7. (c) Houdai, T.; Matsuoka, S.; Morsy, N.; Matsumori, N.; Satake, M.; Murata, M. Tetrahedron 2005, 61, 2795-2802.
8. (d) Morsy, N.; Houdai, T.; Konoki, K.; Matsumori, N.; Oishi, T.; Murata, M. Bioorg. Med. Chem. 2008, 16, 3084-3090.
9. (a) Paul, G. K.; Matsumori, N.; Murata, M.; Tachibana, K. Tetrahedron Lett. 1995, 36, 6279-6282.
10. (b) Morsy, N.; Matsuoka, S.; Houdai, T.; Matsumori, N.; Adachi, S.; Murata, M.; Iwashita, T.; Fujita, T. Tetrahedron 2005, 61, 8606-8610.
11. (c) Echigoyaa, R.; Rhodesb, L.; Oshimaa, Y.; Satakea, M. Harmful Algae 2005, 4, 383-389.
12. (d) Morsy, N.; Houdai, T.; Matsuoka, S.; Matsumori, N.; Adachi, S.; Oishi, T.; Murata, M.; Iwashita, T.; Fujita, T. Bioorg. Med. Chem. 2006, 14, 6548.
13. Matsumori, N.; Kaneno, D.; Murata, M.; Nakamura, H.; Tachibana, K. J. Org. Chem. 1999, 64, 866-876.
14. (a) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
15. (b) Rieser, M. J.; Hui, Y.-H.; Rupprecht, J. K.; Kozlowski, J. F.; Wood, K. V.; McLaughlin, J. L.; Hanson, P. R.; Zhuang, Z.; Hoye, T. R. J. Am. Chem. Soc. 1992, 114, 10203-10213.
16. (c) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
17. (d) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143-2147.
18. Oishi, T.; Kanemoto, M.; Swasono, R.; Matsumori, N.; Murata, M. Org. Lett. 2008, 10, 5203-5206.
19. (a) BouzBouz, S.; Cossy, J. Org. Lett. 2001, 3, 1451-1454.
20. (b) Cossy, J.; Tsuchiya, T.; Ferrie, L.; Reymond, S.; Kreuzer, T.; Colobert, F.; Jourdain, P.; Marko, I. E. Synlett 2007, 2286-2288.
21. (c) Colobert, F.; Kreuzer, T.; Cossy, J.; Reymond, S.; Tsuchiya, T.; Ferrie, L.; Marko, I. E.; Jourdain, P. Synlett 2007, 2351-2354.
22. (a) Flamme, E. M.; Roush, W. R. Org. Lett. 2005, 7, 1411-1414.
23. (b) Hicks, J. D.; Flamme, E. M.; Roush, W. R. Org. Lett. 2005, 7, 5509-5512.
24. (c) Hicks, J. D.; Roush, W. R. Org. Lett. 2008, 10, 681-684.
25. (a) de Vicente, J.; Betzemeier, B.; Rychnovsky, S. D. Org. Lett. 2005, 7, 1853-1856.
26. (b) de Vicente, J.; Huckins, J. R.; Rychnovsky, S. D. Angew. Chem., Int. Ed. 2006, 45, 7258-7262.
27. (c) Huckins, J. R.; de Vicente, J.; Rychnovsky, S. D. Org. Lett. 2007, 9, 4757-4760.
28. (a) Paquette, L. A.; Chang, S.-K. Org. Lett. 2005, 7, 3111-3114.
29. (b) Chang, S.-K.; Paquette, L. A. Synlett 2005, 2915-2918.
30. (c) Bedore, M. W.; Chang, S.-K.; Paquette, L. A. Org. Lett. 2007, 9, 513-516.
31. Dubost, C.; Markó, I. E.; Bryans, J. Tetrahedron Lett. 2005, 46, 4005-4009.
32. (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
33. (b) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K. S.; Kwong, H. L.; Morikawa, K.; Wang, Z. M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768-2771.
34. (a) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974-5976.
35. (b) Gao, Y.; Klunder, J. M.; Hanson, R. M.; Masamune, H.; Ko, S. Y.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
36. (a) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K.; Somers, P. K. Chem. Commun. 1985, 1359-1362.
37. (b) Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517-4552.
38. For recent application to natural product synthesis, see: (a) BouzBouz, S.; Roche, C.; Cossy, J. Synlett 2009, 803-807.
39. (b) Ferrie, L.; Boulard, L.; Pradaux, F.; Bouzbouz, S.; Reymond, S.; Capdevielle, P.; Cossy, J. J. Org. Chem. 2008, 73, 1864-1880.
40. (c) Amans, D.; Bellosta, V.; Cossy, J. Org. Lett. 2007, 9, 1453-1456.
41. Charette, A. B.; Gagnon, A.; Fournier, J.-F. J. Am. Chem. Soc. 2002, 124, 386-387.
42. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
43. (a) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771-1780.
44. (b) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
45. (a) Smith, A. B.; Zheng, J. Tetrahedron 2002, 58, 6455-6471.
46. (b) Jung, M. E.; Light, L. A. Tetrahedron Lett. 1982, 23, 3851-3854.