Synthetic studies towards oxylipins: Total synthesis of Constanolactones A and B

Tetrahedron Letters

Volumn 41, Issue 17, 2000, Pages 3077-3081

  Barloy Da Silva, Catherine ^a   Benkouider, Abdelhamid ^b   Pale, Patrick ^a  

^a CNRS   (France)

^b UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Alkylation; Cyclopropanes; Dienes; Eicosanoids

Indexed keywords

CONSTANOLACTONE A; CONSTANOLACTONE B; CYCLOPROPANE DERIVATIVE; ICOSANOID; OXYLIPIN DERIVATIVE; PLANT EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERISM; RED ALGA; SPECTROSCOPY;

EID: 0034701459     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00343-9     Document Type: Article

References (39)

1. Gerwick, W. H. Chem. Rev. 1993, 93, 1807-1823.
2. Gerwick, W. H.; Nagle, D. G.; Proteau, P. J. Topics in Current Chem. 1993, 167, 117-180.
3. Gerwick, W. H.; Bernart, M. W. In Marine Biotechnology, Vol. I: Pharmaceutical and Bioactive Natural Products; Attaway, D. H.; Zaborsky, O. R., Eds. Eicosanoids and Related Compounds from Marine Algae. Plenum: New York, 1992; p. 101.
4. (a) Nagle, D. G.; Gerwick,W. H. Tetrahedron Lett. 1990, 31, 2995-2999.
5. (b) Nagle, D. G.; Gerwick,W. H. J. Org. Chem. 1994, 59, 7227-7237.
6. Gerwick, W. H. Lipids 1996, 31, 1215-1231.
7. (a) Varadarajan, S.; Mohapatra, D. K.; Datta, A. Tetrahedron Lett. 1998, 39, 5667-5670.
8. (b) White, J. D.; Jensen, M. S. J. Am. Chem. Soc. 1995, 117, 6224-6233.
9. (c) For other approaches to related oxylipins, see: Miyaoka, H.; Shigemoto, T.; Yamada, Y. Heterocycles 1998, 47, 415-428; Nagasawa, T.; Onoguchi, Y.; Matsumoto, T.; Suzuki, K. Synlett 1995, 1023-1024.
10. (c) For other approaches to related oxylipins, see: Miyaoka, H.; Shigemoto, T.; Yamada, Y. Heterocycles 1998, 47, 415-428; Nagasawa, T.; Onoguchi, Y.; Matsumoto, T.; Suzuki, K. Synlett 1995, 1023-1024.
11. White, J. D.; Jensen, M. S. Synlett 1996, 31-33.
12. 10a Benkouider, A.; Renevret, G.; Pale, P., manuscript in preparation.
13. Benkouider, A; Pale, P. J. Chem. Res. (S) 1999, 104-105.
14. (a) Benkouider, A. PhD Thesis, University of Reims-Champagne-Ardenne, Reims, 1994.
15. (b) Barloy-Da Silva, C. PhD Thesis, University L. Pasteur, Strasbourg, 1999.
16. Barloy-Da Silva, C.; Pale, P. Tetrahedron: Asymmetry 1998, 9, 3951-3954.
17. Bellassoued, M.; Ennigrou, R.; Gaudemar, M. J. Organomet. Chem. 1988, 338, 149-158.
18. (a) Mooiver, H. H.; Ettena, K. W. A.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1990, 46, 2991-2998.
19. (b) Brands, K. M. J.; Meekel, A. A. P.; Pandit, U. K. Tetrahedron 1991, 47, 2005-2026.
20. (c) Brandstater, S. M.; Ojima, I.; Hirai, K. Tetrahedron Lett. 1987, 28, 613-616.
21. Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron 1991, 47, 1215-1230.
22. Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081-1083.
23. 14
24. Wetter, H.; Oertle, K. Tetrahedron Lett. 1985, 26, 5515-5518.
25. Chaudhary, S. K.; Hernandez, O. Tetrahedron Lett. 1979, 32, 99-102.
26. Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651-1660.
27. Fleming, I. Bull. Soc. Chem. Fr. 1981, 2, 7-13.
28. Lumbardo, L. Tetrahedron Lett. 1985, 26, 381-384.
29. (a) Mukaiyama, T. Org. React. 1988, 38, 793.
30. (b) Shirai, F.; Nakai, T. Tetrahedron Lett. 1988, 29, 6461-6465.
31. Preliminary results have shown that the diastereoselectivity as well as the α/γ selectivity varied upon the conditions and the catalyst used. Such additions of 1-silyloxy-1-alkoxy dienes to aldehydes are now actively studied in our group. Benkouider, A.; Barloy-Da Silva, C.; Chriqui, Y.; Pale, P., manuscript in preparation.
32. Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G. Tetrahedron Lett. 1987, 28, 5287-5290.
33. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
34. Wipf, P.; Jahn, H. Tetrahedron 1996, 12 854-12 909.
35. Maeta, H.; Hashimoto, T.; Hasegawa, T.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5965-5968.
36. Wipf, P.; Xu, W. Tetrahedron Lett. 1994, 35, 5197-5200.
37. Fürtsner, A. Chem. Rev. 1999, 99, 991-1045.
38. Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885-888.
39. 3).