Synthesis of cyclopentane-containing marine eicosanoid bacillariolide II

Tetrahedron Letters

Volumn 39, Issue 7, 1998, Pages 621-624

  Miyaoka, Hiroaki ^a   Tamura, Masahide ^a   Yamada, Yasuji ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; ICOSANOID;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0032510018     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10660-8     Document Type: Article

References (20)

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2. b) Gerwick, W. H., Biochim., Biophys. Acta., 1994, 1211, 243-255.
3. 2. This organism was previously designated Nitzschia pungens f. multiseries, but which recently has been changed to Pseudo-nitzschia multiseries.
4. 3. a) Wang, R.; Shimizu, Y. J. Chem. Soc., Chem. Commun., 1990, 413-414.
5. b) Wang, R.; Shimizu, Y.; Steiner, J. R.; Clardy, J. J. Chem. Soc., Chem. Commun., 1993, 379-380.
6. c) Zheng, N.; Shimizu, Y. Chem. Commun., 1997, 399-400.
7. 4. Shimizu, Y. Annu. Rev. Microbiol., 1996, 50, 431-465.
8. 5. a) Miyaoka, H.; Shigemoto, T.; Yamada, Y. Tetrahedron Lett., 1996, 41, 7407-7408.
9. b) Miyaoka, H.; Shigemoto, T.; Yamada, Y. Heterocycles, in press.
10. 6. Relative reaction: Eisch, J.J.; Dua, S.K.; Behrooz, M. J. Org. Chem., 1985, 50, 3674-3676.
11. 7. Numbering of compounds is in accordance with that for bacillariolide.
12. 8. Jeffery, T.; Gueugnot, S.; Linstrumelle, G. Tetrahedron Lett., 1992, 33, 5757-5760.
13. 9. Lapitskaya, M. A.; Vasiljeva, L. L.; Pivnitsky, K. K. Synthesis, 1993, 65-66.
14. 10. Saito, S.; Hasegawa, T.; Inaba, M.; Nishida, R.; Fujii, T.; Nomizu, S.; Moriwake, T. Chem. Lett., 1984, 1389-1392.
15. 11. Banfi, L.; Cascio, G.; Guanti, G.; Manghisi, E.; Narisano, E.; Riva, R. Tetrahedron, 1994, 41, 11967-11982.
16. 12. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc., 1987, 109, 5765-5780 and references cited therein.
17. 3) δ 30.0, 30.3, 48.5, 55.1, 56.0, 69.3, 72.6, 72.9, 74.5, 82.2, 95.1, 113.6, 120.0, 128.2, 129.4, 130.1, 130.7, 133.5, 134.4, 135.2, 159.0.
18. (formula presented)
19. H 7.81).
20. 3OD) δ 14.7, 21.5, 25.5, 26.4, 26.5, 27.0, 36.9, 45.3, 52.6, 73.4, 77.7, 127.5, 128.1, 128.4, 128.8, 129.6, 129.9, 132.9, 133.1, 183.6.