Total synthesis of Brevetoxin-B

Journal of the American Chemical Society

Volumn 126, Issue 44, 2004, Pages 14374-14376

  Matsuo, Goh ^a   Kawamura, Koji ^a   Hori, Nobuyuki ^a   Matsukura, Hiroko ^a   Nakata, Tadashi ^a,b  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BREVETOXIN; BREVETOXIN B; NEUROTOXIN; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; NONHUMAN; REACTION ANALYSIS; RED TIDE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; TOXIN ANALYSIS;

ANIMALS; DINOFLAGELLIDA; MARINE TOXINS; OXOCINS;

EID: 7744246249     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0449269     Document Type: Article

References (31)

1. Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773.
2. Total synthesis of 1: (a) Nicolaou, K. C.; Rutjes, F. P. J. T.; Theodorakis, E. A.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 1173.
3. (b) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Sato, M.; Tiebes, J.; Xiao, X.-Y.; Hwang, C.-K.; Duggan, M. E.; Yang, Z.; Couladouros, E. A.; Sato, F.; Shin, J.; He, H.-M.; Bleckman, T. J. Am. Chem. Soc. 1995, 117, 10239.
4. (c) Nicolaou, K. C.; Rutjes, F. P. J. T.; Theodorakis, E. A.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 10252.
5. For synthetic approaches toward 1, see: (d) Matsuo, G.; Matsukura, H.; Hori, N.; Nakata, T. Tetrahedron Lett. 2000, 41, 7673.
6. (e) Matsuo, G.; Hori, N.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 2000, 41, 7677.
7. (f) Matsukura, H.; Hori, N.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 2000, 41, 7681.
8. (g) Kadota, I.; Nishina, N.; Hishii, H.; Kikuchi, S.; Yamamoto, Y. Tetrahedron Lett. 2003, 44, 7929.
9. Sakata, H.; Aoki, Y.; Kuwajima, I. Tetrahedron Lett. 1990, 31, 1161.
10. For stereochemical determination of the α-methyl group, see Supporting Information.
11. (a) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811.
12. (b) Hori, N.; Matsukura, H.; Nakata, T. Org. Lett. 1999, 1, 1099.
13. (c) Matsuo, G.; Hori, N.; Nakata, T. Tetrahedron Lett. 1999, 40, 8859.
14. (d) Hori, N.; Matsukura, H.; Matsuo, G. Tetrahedron 2002, 58, 1853.
15. Winterfeldt E, Preuss H. Chem. Ber. 1966, 99, 450.
16. 13C NMR, NOE, and HMBC). See Supporting Information.
17. 2-induced cyclization.
18. For a review, see: Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986.
19. Diastereoselectivity of this reduction was ca. 9:1.
20. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5976.
21. Miyashita, M.; Yoshikoshi, A.; Grieco, P. A. J. Org. Chem. 1977, 42, 3772.
22. Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330.
23. At this stage, the corresponding minor β-epoxide isomer did not cyclize.
24. For a review, see: Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
25. Nokami, J.; Ogawa, H.; Miyamoto, S.; Mandai, T.; Wakabayashi, S.; Tsuji, J. Tetrahedron Lett. 1988, 29, 5181.
26. Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517.
27. Corey, E. J.; Ha, D.-C. Tetrahedron Lett. 1988, 29, 3171.
28. Krohn, K.; Börner, G. J. Org. Chem. 1991, 56, 6038.
29. Molander, G. A.; Etter, J. B. J. Am. Chem. Soc. 1987, 109, 6556.
30. Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365.
31. Oxidation of 41 under the same reaction conditions gave 40 in 63% yield (86% based on the consumed 41).