Biosynthetic studies of amphidinolide J: Explanation of the generation of the unusual odd-numbered macrocyclic lactone

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 16, 1995, Pages 1639-1640

  Kobayashi, Jun'ichi ^a   Takahashi, Miho ^a   Ishibashi, Masami ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; AMPHIDINOLIDE J; CARBON 13; MACROLIDE; POLYKETIDE; UNCLASSIFIED DRUG;

ANTIBIOTIC BIOSYNTHESIS; ARTICLE; CHEMICAL STRUCTURE; DINOFLAGELLATE; FEEDING; NONHUMAN; PARASITE CULTIVATION;

EID: 0029145229     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39950001639     Document Type: Article

References (33)

1. Macrolide Antibiotics, ed. S. Omura, Academic, New York, 1984.
2. J. Kobayashi and M. Ishibashi, Chem. Rev., 1993, 93, 1753.
3. M. Ishibashi, H. Ishiyama and J. Kobayashi, Tetrahedron Lett. 1994, 35, 8241 and references cited therein.
4. I. Bauer, L. Maranda, Y. Shimizu, R.W. Peterson, L. Cornell, J.R. Steiner and J. Clardy, J. Am. Chem. Soc., 1994, 116, 2657.
5. I. Bauer, L. Maranda, K.A. Young, Y. Shimizu, C. Fairchild, L. Cornell, J. MacBeth and S. Huang, J. Org. Chem., 1995, 60, 1084.
6. J. Kobayashi, N. Yamaguchi and M. Ishibashi, Tetrahedron Lett., 1994, 35, 7049.
7. D. O’Hagan, Nut. Prod. Rep., 1995, 12, 1.
8. For reviews see: Y. Shimizu, Chem. Rev., 1993, 93, 1685.
9. M.J. Garson, Chem. Rev., 1993, 93, 1699.
10. Brevetoxins: M.S. Lee, D.J. Repeta, K. Nakanishi and M.G. Zagorski, J. Am. Chem. Soc., 1986, 108, 7855.
11. H.-N. Chou and Y. Shimizu, J. Am. Chem. Soc., 1987, 109, 2184.
12. M.S. Lee, G.-W. Qin, K. Nakanishi and M.G. Zagorski, J. Am. Chem. Soc. 1989, 109, 6234.
13. Okadaic acid and dinophysistoxins: K. Torigoe and T. Yasumoto, Tennen Yuki Kagobutsu Toronhi Yoshishu, 1991, 33, 525.
14. F.J. Schmitz and T. Yasumoto, J. Nut. Prod., 1991, 54, 1469.
15. M. Norte, A. Padilla and J.J. FernBndez, Tetrahedron Lett. 1994, 35, 1441.
16. M. Norte, A. Padilla, J.J. FernBndez, M.L. Souto, Tetrahedron, 1994, 50, 9175.
17. J. Needham, J.L. McLachlan, J.A. Water and J.L.C. Wright, J. Chem. Soc., Chem. Commun., 1994, 2599.
18. Marine and terrestrial cyanobacterial polyketides: S. Carmeli, R.E. Moore, G.M.L. Patterson and W.Y. Yoshida, Tetrahedron Lett., 1993, 34, 5571.
19. T. Hemscheidt, M.P. Puglisi, L.K. Larsen, G.M.L. Patterson, R.E. Moore, J.L. Rios and J. Clardy, J. Org. Chem., 1994, 59, 3467.
20. J. Needham, R.J. Andersen and M.T. Kelly, J. Chem. Soc., Chem. Commun., 1992, 1367.
21. J. Needham, M.T. Kelly, M. Ishige and R.J. Andersen, J. Org. Chem., 1994, 59, 2058.
22. Ascidian alkaloids: B. Steffan, K. Brix and W. Putz, Tetrahedron 1993, 49, 6223.
23. G.Q. Shen and B.J. Baker, Tetrahedron Lett., 1994, 35, 1141.
24. J. Kobayashi, M. Sato and M. Ishibashi, J. Org. Chem., 1993, 58, 2645.
25. D.G.I. Kingston, M.X. Kolpak, J.W. LeFevre and I. Borup-Grochtmann, J. Am. Chem. Soc., 1983, 105, 5106.
26. W. Trowitzsch, K. Gerth, V. Wray and G. Hofle, J. Chem. Soc., Chem. Commun., 1983, 1174.
27. For those possessing vicinal one-carbon branches: e.g., D. Uemura, K. Takahashi, T. Yamamoto, C. Katayama, J. Tanaka, Y. Okumura and Y. Hirata, J. Am. Chem. Soc., 1985, 107, 4796.
28. M. Murakami, K. Makabe, K. Yamaguchi, S. Konosu and M.R. Walchli, Tetrahedron Lett., 1988, 29, 1149.
29. N.B. Perry, J.W. Blunt, M.H.G. Munro and L.K. Pannell, J. Am. Chem. Soc., 1988, 110, 4850.
30. S. Sakemi, T. Ichiba, S. Kohmoto, G. Saucy and T. Higa, J. Am. Chem. Soc., 1988, 110, 4851.
31. M. Murata, A.-M. Legrand, Y. Ishibashi, M. Fukui and T. Yasumoto, J. Am. Chem. Soc., 1990, 112, 4380.
32. M. Murata, H. Naoki, S. Matsunaga, M. Satake and T. Yasumoto, J. Am. Chem. Soc., 1994, 116, 7098.
33. I. Bauer, L. Maranda, K.A. Young, Y. Shimizu and S. Huang, Tetrahedron Lett., 1995, 36, 991.