Biomimetic cyclisation of prebrevetoxin polyepoxide models

Tetrahedron Letters

Volumn 40, Issue 16, 1999, Pages 3251-3254

  Kelly, David R ^a   Nally, James ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIHYDROXY 4 HEXENE; 1,3 DIHYDROXY 4 METHYL 4 HEXENE; BREVETOXIN; EPOXIDE; ETHYLENE OXIDE DERIVATIVE; HYDROXYL GROUP; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; EPOXIDATION; RACEMIC MIXTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033574560     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00376-7     Document Type: Article

References (23)

1. Prasad, A. V.; Shimizu, Y. J. Am. Chem. Soc. 1989, 111, 6476-6477.
2. Zagorski, M. G.; Nakanishi, K.; Qin, G.; Lee, M. S. J. Org. Chem. 1988, 53, 4157-4158.
3. Shimizu, Y.; Bando, H.; Chou, H.-N.; Van Duyne, G.; and Clardy, J. C. J. Chem. Soc., Chem. Commun. 1986, 1656-1658.
4. Golik, J.; James, J. C.; Nakanishi, K. Tetrahedron Lett. 1982, 23, 2535-2538.
5. Chou, H.-N.; Shimizu, Y. Tetrahedron Lett. 1982, 23, 5521-5524.
6. Chou, H.-N.; Shimizu, Y.; Van Duyne G.; Clardy, J. Tetrahedron Lett. 1985, 26, 2865.
7. An alternative nomenclature is commonly used by biochemists see Baden, D. G. FASEB J. 1989, 3, 1807-1817.
8. Ishida, H.; Nozawa, A.; Tororibe, K.; Muramatsu, N.; Nukaya, H.; Tsuji, K.; Yamaguchi, K.; Yasumoto, T.; Kaspar, H.; Berkett, N.; Kosuge, T. Tetrahedron 1995, 36, 725-728.
9. Murata, K.; Satake, M.; Naoki, H.; Kaspar, H. F.; Yasumoto, T. Tetrahedron 1998, 54, 735-742.
10. Morohashi, A.; Satake, N.; Murata, K.; Naoki, H.; Kaspar, H. J.; Yasumoto, T. Tetrahedron Lett. 1995, 36, 8995-8998. It may equally well be argued that BTX-B3 is the product of an aborted anabolic polycyclisation rather than catabolic degradation of BTX-B.
11. Nicolaou, K. C. Chem. Brit. 1985, 813-819; for a review see Kelly, D. R. in The Chemistry of natural Products, Thompson, R. H. (ed), Blackie, Glasgow, 2nd edition, 1993, 382-441.
12. Nicolaou, K. C. Chem. Brit. 1985, 813-819; for a review see Kelly, D. R. in The Chemistry of Natural Products, Thompson, R. H. (ed), Blackie, Glasgow, 2nd edition, 1993, 382-441.
13. Na, J.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 9204-9205 and references therein.
14. For the previous paper in this series on biomimetic cyclisations of brevetoxins see Kelly, D. R.; Nally, J. Tetrahedron Lett. 1999, 40, 2209-2212.
15. McCain, J. H.; Marcus, E. J. Org. Chem. 1970, 35, 2414-52415.
16. van der Goorbergh, J. A. M.; Nonneman, L. E. Y.; van der Gen, A. Recueil Trav. Chim. Pays Bas 1985, 104, 277-281.
17. Chenault, H. K.; Mandes, R. F. Tetrahedron Lett. 1997, 53, 11033-11038.
18. Mihailovic, M. L.; Pavlovic, N.; Gojkovic, S. Bull. Soc. Chim. Beograd 1975, 40, 309-319.
19. 3SnH gave the cis-diastereoisomer 10b. Full details will be reported elsewhere.
20. Mihelich, E. D. Tetrahedron Lett. 1979, 4729-4732; Rossiter, R., Verhoeven, T. R.; Sharpless, K. B.ibid 4733-4736.
21. Mihelich, E. D. Tetrahedron Lett. 1979, 4729-4732; Rossiter, R., Verhoeven, T. R.; Sharpless, K. B. ibid 4733-4736.
22. Nicolaou, K. C.; Duggan, M. E.; Hwang, C. K.; Somers, P. K. J. Chem. Soc., Chem. Commun. 1985, 1359-1362.
23. Wuts, P. G. M.; D'Costa, R.; Butler, W. J. Org. Chem. 1984, 49, 2582-2588.