Stereoselective synthesis of the C(53)-C(67) polyene fragment of amphidinol 3

Synlett

Volumn , Issue 15, 2007, Pages 2351-2354

  Colobert, Françoise ^a   Kreuzer, Thomas ^a   Cossy, Janine ^b   Reymond, Sébastien ^b   Tsuchiya, Tomoki ^b   Ferrié, Laurent ^b   Marko, Istvan E ^c   Jourdain, Pierre ^c  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b CNRS   (France)

^c UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

Addition reactions; Amphidinol 3; Natural products; Reductive elimination; Total synthesis

Indexed keywords

1 (TERT BUTYLDIPHENYLSILANYLOXY) 12 (TERT BUTYLDIMETHYLSILANYLOXY)DODECA 4,6,8 TRIENE; 1 (TERT BUTYLDIPHENYLSILANYLOXY)PENTADECA 4,6,8,12,14 PENTAENE; ACETYLENE; AMPHIDINOL 3; CARBON; POLYENE; POLYETHER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; OXIDATION REDUCTION REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 34948829004     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-985601     Document Type: Article

References (42)

1. (a) Shimizu, Y. Chem. Rev. 1993, 1685.
2. (b) Yasumoto, T.; Murata, M. Chem. Rev. 1193, 1897.
3. Echigoya, R.; Rhodes, L.; Oshima, Y.; Satake, M. Harmful Algae 2005, 4, 383.
4. Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1991, 113, 9859.
5. (a) Houdai, T.; Matsuoka, S.; Morsy, N.; Matsumori, N.; Satake, M.; Murata, M. Tetrahedron 2005, 61, 2795.
6. (b) Paul, G. K.; Matsumori, N.; Nonoki, K.; Sasaki, M.; Murata, M.; Tachibana, K. In Harmful and Toxic Algal Blooms.; Yasumoto, T.; Oshima, Y.; Fukuyo, Y., Eds.; Proceedings of the Seventh International Conference on Toxic Phytoplankton, UNESCO: Sendai, Japan, 1996, 503.
7. (a) Murata, M.; Matsuoka, S.; Matsumori, N.; Paul, G. K.; Tachibana, K. J. Am. Chem. Soc. 1999, 121, 870.
8. (b) Matsumori, N.; Kaneno, D.; Murata, M.; Nakamura, H.; Tachibana, K. J. Org. Chem. 1999, 64, 866.
9. (a) Paquette, L. A.; Chang, S.-K. Org. Lett. 2005, 7, 3111.
10. (b) Chang, S.-K.; Paquette, L. A. Synlett 2005, 2915.
11. (c) Bedorre, M. W.; Chang, S.-K.; Paquette, L. A. Org. Lett. 2007, 9, 513.
12. (a) de Vicente, J.; Betzemeier, B.; Rychnovsky, S. D. Org. Lett. 2005, 7, 1853.
13. (b) de Vicente, J.; Huckins, J. R.; Rychnovsky, S. D. Angew. Chem. Int. Ed. 2006, 45, 7258.
14. (a) Flamme, E. M.; Roush, W. R. Org. Lett. 2005, 7, 1411.
15. (b) Hicks, J. D.; Flamme, E. D.; Roush, W. R. Org. Lett. 2005, 7, 5509.
16. BouzBouz, S.; Cossy, J. Org. Lett. 2001, 7, 1451.
17. Dubost, C.; Markó Bryans, J. Tetrahedron Lett. 2005, 46, 4005.
18. Cossy, J.; Tsuchiya, T.; Ferrié, L.; Reymond, S.; Kreuzer, T.; Colobert, F.; Jourdain, P.; Markó, I. Synlett 2001, in press.
19. (a) Solladié, G.; Urbano, A.; Stone, G. B. Synlett 1993, 548.
20. (b) Solladié, G.; Urbano, A.; Stone, G. B. Tetrahedron Lett. 1993, 34, 6489.
21. (c) Solladié, G.; Colobert, F.; Kalaï, C. Tetrahedron Lett. 2000, 41, 4197.
22. (d) Solladié, G.; Kalaï, C.; Adamy, M.; Colobert, F. Tetrahedron Lett. 1997, 39, 6917.
23. (e) Solladié, G.; Somny, F.; Colobert, F. Tetrahedron: Asymmetry 1997, 8, 801.
24. (f) Solladié, G.; Adamy, M.; Colobert, F. J. Org. Chem. 1996, 61, 4369.
25. Mc Dougal, P. G.; Rico, J. G.; Oh, Y.-I.; Condom, B. D. J. Org. Chem. 1986, 51, 3388.
26. Nacro, K.; Baltas, M.; Gorrichon, L. Tetrahedron 1999, 55, 14013.
27. Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651.
28. Taillier, C.; Gille, B.; Bellosta, V.; Cossy, J. J. Org. Chem. 2005, 70, 2097.
29. (a) Holmes, A. B.; Jennings-White, C. L. D.; Schulthess, A. H.; Akinde, B.; Walton, D. R. M. J. Chem. Soc., Chem. Commun. 1979, 840.
30. (b) Kraus, G. A.; Bae, J. Tetrahedron Lett. 2003, 44, 5505.
31. (c) For a review, see: Kusumoto, T.; Hiyama, T. Rev. Heteroat. Chem. 1994, 11, 143.
32. (a) Boland, W.; Schröer, N.; Sieler, C.; Feigel, N. Helv. Chim. Acta 1987, 70, 1025.
33. (b) See ref. 12b and 12e.
34. 1H-decoupled NMR spectra resulted in a coupling constant consistent with E-olefins (J = 14.1 Hz).
35. Prakash, C.; Saleh, S.; Blair, I. A. Tetrahedron Lett. 1989, 30, 19.
36. Jung, M. E.; Piizzi, G. J. Org. Chem. 2002, 67, 3911.
37. Takai, S.; Isobe, M. Org. Lett. 2002, 4, 1183.
38. (a) Gómez, A. M.; López, J. C.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3859.
39. (b) Hong, S.-P.; Yoon, S.-J.; Yu, B.-C. Tetrahedron Lett. 2005, 46, 779.
40. (c) van Boxtel, L. J.; Körbe, S.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2001, 2283.
41. (a) Amafor, M.; Ariza, X.; Garcia, J.; Sevilla, S. Org. Lett. 2002, 4, 4511.
42. (b) See ref. 12a.