Diastereoselective Synthesis of the GH Ring Part of Ciguatoxin

Synlett

Volumn 1997, Issue 3, 1997, Pages 307-309

  Atsuta, Hiroyuki ^a   Fujiwara, Kenshu ^a   Murai, Akio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001939879     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-777     Document Type: Article

References (28)

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8. For other synthetic works, see: E. Alvarez, M. T. Díaz, R. Pérez, J. L. Ravero, A. Reguerio, J. A. Vera, D. Zurita, and J. D. Martín, J. Org. Chem., 59, 2848 (1994); M. Sasaki, M. Inoue, and K. Tachibana, J. Org. Chem., 59, 715 (1994); H. Oguri, S. Hishiyama, T. Oishi, and M. Hirama, Synlett., 1252 (1995); S. Hosokawa and M. Isobe, Synlett, 351 (1996); T. Oka, K. Fujiwara, and A. Murai, Tetrahedron, 52, 12091 (1996); and other references cited there.
9. For other synthetic works, see: E. Alvarez, M. T. Díaz, R. Pérez, J. L. Ravero, A. Reguerio, J. A. Vera, D. Zurita, and J. D. Martín, J. Org. Chem., 59, 2848 (1994); M. Sasaki, M. Inoue, and K. Tachibana, J. Org. Chem., 59, 715 (1994); H. Oguri, S. Hishiyama, T. Oishi, and M. Hirama, Synlett., 1252 (1995); S. Hosokawa and M. Isobe, Synlett, 351 (1996); T. Oka, K. Fujiwara, and A. Murai, Tetrahedron, 52, 12091 (1996); and other references cited there.
10. For other synthetic works, see: E. Alvarez, M. T. Díaz, R. Pérez, J. L. Ravero, A. Reguerio, J. A. Vera, D. Zurita, and J. D. Martín, J. Org. Chem., 59, 2848 (1994); M. Sasaki, M. Inoue, and K. Tachibana, J. Org. Chem., 59, 715 (1994); H. Oguri, S. Hishiyama, T. Oishi, and M. Hirama, Synlett., 1252 (1995); S. Hosokawa and M. Isobe, Synlett, 351 (1996); T. Oka, K. Fujiwara, and A. Murai, Tetrahedron, 52, 12091 (1996); and other references cited there.
11. For other synthetic works, see: E. Alvarez, M. T. Díaz, R. Pérez, J. L. Ravero, A. Reguerio, J. A. Vera, D. Zurita, and J. D. Martín, J. Org. Chem., 59, 2848 (1994); M. Sasaki, M. Inoue, and K. Tachibana, J. Org. Chem., 59, 715 (1994); H. Oguri, S. Hishiyama, T. Oishi, and M. Hirama, Synlett., 1252 (1995); S. Hosokawa and M. Isobe, Synlett, 351 (1996); T. Oka, K. Fujiwara, and A. Murai, Tetrahedron, 52, 12091 (1996); and other references cited there.
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17. K. Tsushima, K. Araki, and A. Murai, Chem. Lett., 1313 (1989); F. Feng and A. Murai, Chem. Lett., 1587 (1992).
18. 2, r.t., 1 day; (d) KH, THF, r.t., 1 day.
19. R. W. Murray, Chem. Rev., 89, 1187 (1989); W. Adam, L. Hadjiarapoglou and X. Wang, Tetrahedron Lett., 30, 6947 (1989).
20. R. W. Murray, Chem. Rev., 89, 1187 (1989); W. Adam, L. Hadjiarapoglou and X. Wang, Tetrahedron Lett., 30, 6947 (1989).
21. 11
22. T. Morita, Y. Okamoto, and H. Sakurai, Tetrahedron Lett., 21, 835 (1980); A. Hosomi and H. Sakurai, Chem. Lett., 85 (1981).
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24. 1H-NMR spectrum. The C6-epimer of 21 was not given from the C6-epimer of 20b under several conditions.
25. 3), δ(ppm) 7.26-7.37 (10H, m), 4.57 (1H, d, J = 12 Hz), 4.51 (1H, d, J = 12 Hz), 4.43 (1H, d, J = 12 Hz), 4.42 (1H, d, J = 12 Hz), 4.15 (1H, dd, J = 3, 11 Hz), 3.91 (1H, dt, J = 1, 7 Hz), 3.70 (1H, dd, J = 6, 11 Hz), 3.44-3.60 (3H, m), 2.63 (1H, ddd, J = 2, 10, 19 Hz), 2.51 (1H, ddd, J = 9, 11, 19 Hz), 2.00 (1H, ddd, J = 3, 6, 15 Hz), 1.63-1.98 (6H, m), 1.34 (3H, s), 0.92 (9H, s), 0.18 (3H, s), and 0.13 (3H, s).
26. 6), δ(ppm) 7.34 (2H, d, J = 8 Hz), 7.30 (2H, d, J = 7 Hz), 7.15-7.20 (5H, m), 7.06-7.11 (1H, m), 4.47 (1H, d, J = 12 Hz), 4.35 (1H, d, J = 12 Hz), 4.31 (1H, d, J = 12Hz), 4.29 (1H, dd, J = 3, 11 Hz), 4.28 (1H, d, J = 12 Hz), 4.09 (1H, br dd, J = 5, 9 Hz), 3.55 (1H, dd, J = 5, 11 Hz), 3.50 (1H, ddd, J = 6, 8, 9 Hz), 3.37-3.44 (3H, m), 3.26 (1H, dt, J = 2, 12Hz), 2.01 (1H, ddd, J = 3, 6, 15 Hz), 1.90 (1H, ddd, J = 2, 11, 15 Hz), 1.54-1.72 (3H, m), 1.48 (1H, br ddt, J = 4, 12, 12 Hz), 1.34 (3H, s), 1.25-1.39 (1H, m), 1.13 (9H, s), 1.10-1.18 (1H, m), 0.32 (3H, s), and 0.29 (3H, s).
27. The results of differential NOE experiments. (Matrix Presented)
28. E. J. Corey, R. K. Bakshi, S. Shibata, C. P. Chen, and K. Singh, J. Am. Chem. Soc., 109, 7925 (1987) .