Total synthesis of brevetoxin B

Journal of the American Chemical Society

Volumn 127, Issue 25, 2005, Pages 9246-9250

  Kadota, Isao ^a   Takamura, Hiroyoshi ^a   Nishii, Hiroki ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CATALYSTS; ETHERS; OXIDATION; REACTION KINETICS;

ALLYLATION; BREVETOXINS; CHLOROSULFIDE; LEWIS ACID;

SYNTHESIS (CHEMICAL);

ACETAL; ALCOHOL; ALKADIENE; ALPHA ACETOXY ETHER; ALPHA CHLOROSULFIDE; BREVETOXIN B; ETHER DERIVATIVE; HEXACYCLINE; LEWIS ACID; NEUROTOXIN; SULFIDE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYST; OXIDATION; RING CLOSING METATHESIS; SYNTHESIS;

MARINE TOXINS; MOLECULAR CONFORMATION; OXOCINS; STEREOISOMERISM;

EID: 21244492227     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja051171c     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, 6773-6775.
2. (a) Nicolaou, K. C.; Rutjes, F. P. J. T.; Theodorakis, E. A.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 1173-1174.
3. (b) Nicolaou, K. C.; Rutjes, F. P. J. T.; Theodorakis, E. A.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 10252-10263.
4. (c) Matsuo, G.; Kawamura, K.; Hori, N.; Matsukura, H.; Nakata, T. J. Am. Chem. Soc. 2004, 126, 14374-14376.
5. Kadota, I.; Ohno, A.; Matsuda, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 3562-3566.
6. For the preparation of compounds 5 and 6, see Supporting Information.
7. Kadota, I.; Takamura, H.; Sato, K.; Yamamoto, Y. J. Org. Chem. 2002, 67, 3494-3498.
8. For the palladium-catalyzed coupling of alkylzinc reagents, see: Negishi, E.; King, A. O.; Okukado, N. J. Org. Chem. 1977, 42, 1821-1823.
9. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
10. Kadota, I.; Sakaihara, T.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 3195-3198.
11. (a) Dahanukar, V. H.; Rychnovsky, S. D. J. Org. Chem. 1996, 61, 8317-8320.
12. (b) Kopecky, D. J.; Rychnovsky, S. D. J. Org. Chem. 2000, 65, 191-198.
13. (c) Kopecky, D. J.; Rychnovsky, S. D. Org. Synth. 2003, 80, 177-183.
14. The acetates A and B were obtained in 51 and 79% yields, respectively. (Diagram presentation)
15. (a) Inoue, M.; Wang, G.-X.; Wang, J.; Hirama, M. Org. Lett. 2002, 4, 3439-3442.
16. (b) Inoue, M.; Miyazaki, K.; Uehara, H.; Maruyama, M.; Hirama, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12013-12018.
17. Nakagawa, I.; Hata, T. Tetrahedron Lett. 1975, 1409-1412.
18. Mukaiyama, T.; Sugaya, T.; Marui, S.; Nakatsuka, T. Chem. Lett. 1982, 1555-1558.
19. MacAuliffe, J. C.; Hindsgaul, O. Synlett 1998, 307-309.
20. The yield is based on the alcohol 5.
21. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
22. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
23. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
24. Construction of the A ring moiety via ring-closing metathesis has been reported by Nakata; see ref 2c.
25. For the preliminary study on the synthesis and coupling of the JK ring fragment, see: Kadota, I.; Nishina, N.; Nishii, H.; Kikuchi, S.; Yamamoto, Y. Tetrahedron Lett. 2003, 44, 7929-7932.
26. Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517-4552.
27. Pétrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910-912.
28. The Grignard reaction of the hydroxy aldehyde gave poor results.
29. The benzylidene acetal of 34 was unstable under the reaction conditions which were used in the next C-glycosidation.
30. The direct introduction of the C4 unit has been reported by Nakata: Matsukura, H.; Hori, N.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 2000, 41, 7681-7684.
31. Kadota, I.; Takamura, H.; Sato, K.; Ohno, A.; Matsuda, K.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 11893-11899.