Synthetic studies on ciguatoxin [1]; construction of the spiro acetal part (C46-C55)

Tetrahedron

Volumn 54, Issue 1-2, 1998, Pages 1-20

  Oka, Takahiro ^a   Murai, Akio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CIGUATOXIN; SPIRO COMPOUND;

ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031986249     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10253-8     Document Type: Article

References (40)

1. 1. M. Murata, A. M. Legrand, Y. Ishibashi, M. Fukai, and T. Yasumoto, J. Am. Chem. Soc., 1990, 112, 4380; the complete structure of ciguatoxin has recently been determined. M. Satake, A. Morohashi, and T. Yasumoto, The 38th Symposium on the Chemistry of Natural Products, Japan, Sendai, 1996, Abst., pp. 481-486.
2. 1. M. Murata, A. M. Legrand, Y. Ishibashi, M. Fukai, and T. Yasumoto, J. Am. Chem. Soc., 1990, 112, 4380; the complete structure of ciguatoxin has recently been determined. M. Satake, A. Morohashi, and T. Yasumoto, The 38th Symposium on the Chemistry of Natural Products, Japan, Sendai, 1996, Abst., pp. 481-486.
3. 2. For synthetic studies of ciguatoxin, see: a) E. Alvarez, M. T. Díaz, R. Pérez, and J. D. Martín, Tetrahedron Lett., 1991, 32, 2241;
4. b) E. Alvarez, D. Zurita, and J. D. Martín, ibid., 1991, 32, 2245;
5. c) M. Zárraga, and J. D. Martín, ibid., 1991, 32, 2249;
6. d) E. Alvarez, M. L. Rodríguez, D. Zurita, and J. D. Martín, ibid., 1991, 32, 2253;
7. e) O. Sato and M. Hirama, Synlett, 1992, 705;
8. f) E. Alvarez, M. Rico, M. L. Rodríguez, D. Zurita, and J. D. Martín, Tetrahedron Lett., 1992, 33, 3385;
9. g) J. L. Ravelo, A. Regueiro, and J. D. Martín, ibid., 1992, 33, 3389;
10. h) M. A. Soler, J. M. Palazón, and V. S. Martín, ibid., 1993, 34, 5471;
11. i) M. Sasaki, A. Hasegawa, and K. Tachibana, ibid., 1993, 34, 8489;
12. j) T. Oka and A. Murai, Chem. Lett., 1994, 1611;
13. k) M. Sasaki, M. Inoue, and K. Tachibana, J. Org. Chem., 1994, 59, 715;
14. l) E. Alvarez, M. T. Díaz, R. Pérez, J. L. Ravelo, A. Regueiro, J. A. Vera, D. Zurita, and J. D. Martín, ibid., 1994, 59, 2848;
15. m) E. Alvarez, M. T. Díaz, L. Hanxing, and J. D. Martín, J. Am. Chem. Soc., 1995, 117, 1437;
16. n) S. Hosokawa and M. Isobe, Synlett, 1995, 1179;
17. o) idem., ibid., 1996, 351;
18. p) T. Oishi, M. Shoji, K. Maeda, N. Kumahara, and M. Hirama, ibid., 1996, 1165;
19. q) H. Oguri, S. Hishiyama, T. Oishi and M. Hirama, ibid., 1996, 1252;
20. r) M. Isobe, S. Hosokawa, and K. Kira, Chem. Lett., 1996, 473;
21. s) T. Oka, K. Fujiwara, and A. Murai, Tetrahedron, 1996, 37, 12091;
22. t) E. Alvarez, M. Delgado, M. T. Díaz, L. Hanxing, R. Pérez, and J. D. Martín, Tetrahedron Lett., 1996, 37, 2865;
23. u) J. L. Ravelo, A. Regueiro, E. Rodríguez, J. Vera, and J. D. Martín, ibid., 1996, 37, 2869;
24. v) E. Alvarez, R. Pérez, M. Rico, R. M. Rodríguez, and J. D. Martín, J. Org. Chem., 1996, 61, 3003;
25. w) H. Atsuta, K. Fujiwara, and A. Murai, Synlett, 1997, 307;
26. x) H. Oguri, S. Hishiyama, O. Sato, T. Oishi, M. Hirama, M. Murata, T. Yasumoto, and N. Harada, Tetrahedron, 1997, 53, 3057;
27. y) M. Inoue, M. Sasaki, and K. Tachibana, Tetrahedron Lett., 1997, 38, 1611;
28. z) T. Oishi, K. Maeda, and M. Hirama, J. Chem. Soc., Chem. Commum., 1997, 1289;
29. aa) T. Oishi, M. Shoji, N. Kumahara, and M. Hirama, Chem. Lett., 1997, 845;
30. bb) T. Oka, K. Fujiwara, and A. Murai, Tetrahedron Lett., in press.
31. 3. Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, and K. B. Sharpless, J. Am. Chem. Soc., 1987, 109, 5765.
32. 4. a) T. Suzuki, H. Saimoto, H. Tomioka, K. Oshima, and H. Nozaki, Tetrahedron Lett., 1982, 23, 3597;
33. b) W. R. Roush, M. A. Adam, S. M. Peseckis, ibid., 1983, 24, 1377.
34. 5. H. Nagaoka and Y. Kishi, Tetrahedron, 1981, 37, 3873.
35. 6. I. Ohtani, T. Kuai, Y. Kashman, and H. Kakisawa, J. Am. Chem. Soc., 1991, 113, 4092.
36. 7. D. J. Cram and F. A. A. Elhafez, J. Am. Chem. Soc., 1952, 74, 5828.
37. 8. J. Inagawa, K. Hirata, S. Saeki, T. Katsuki, and M. Yamaguchi, Bull. Chem. Soc. Jpn., 1979, 52, 1989.
38. 9. For the prediction of the stereochemistry in the major osmylation products of allylic alcohol systems, see J. K. Cha, W. J. Christ, and Y. Kishi, Tetrahedron, 1984, 40, 2247.
39. 10. K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K. -S. Jeong, H. -L. Kwong, K. Morikawa, Z. -M. Wang, D. Xu, and X. -L. Zhang, J. Org. Chem., 1992, 57, 2768.
40. 2O (1:1) at 0 °C → r.t. for 48 h gave a complex mixture.