Convergent synthesis of the ABCDE ring framework of ciguatoxin

Chemical Communications

Volumn , Issue 12, 1999, Pages 1063-1064

  Maeda, Kenji ^a   Oishi, Tohru ^a   Oguri, Hiroki ^a   Hirama, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CIGUATOXIN;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0033591751     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a903063h     Document Type: Article

References (24)

1. M. Murata, A. M. Legrand, Y. Ishibashi, M. Fukui and T. Yasumoto, J. Am. Chem. Soc., 1990, 112, 4380; M. Satake, A. Morohashi, H. Oguri, T. Oishi, M. Hirama, N. Harada and T. Yasumoto, J. Am. Chem. Soc., 1997, 119, 11325.
2. M. Murata, A. M. Legrand, Y. Ishibashi, M. Fukui and T. Yasumoto, J. Am. Chem. Soc., 1990, 112, 4380; M. Satake, A. Morohashi, H. Oguri, T. Oishi, M. Hirama, N. Harada and T. Yasumoto, J. Am. Chem. Soc., 1997, 119, 11325.
3. For recent synthetic studies, see: T. Oishi, M. Shoji, K. Maeda, N. Kumahara and M. Hirama, Synlett, 1996, 1165; T. Oishi, K. Maeda and M. Hirama, Chem. Commun., 1997, 1289; T. Oishi, M. Shoji, N. Kumahara and M. Hirama, Chem. Lett., 1997, 845; T. Oishi, Y. Nagumo and M. Hirama, Synlett, 1997, 307; S. Hosokawa and M. Isobe, Synlett, 1996, 351; T. Oka, K. Fujiwara and A. Murai, Tetrahedron, 1996, 37, 1179; E. Alvarez, M. Delgado, M. T. Díaz, L. Hanxing, R. Pérez and J. D. Martín, Tetrahedron Lett., 1996, 37, 2865; J. L. Ravelo, A. Regueiro, E. Rodríguez, J. A. Vera and J. D. Martín, Tetrahedron Lett., 1996, 37, 2869; S. Hosokawa, K. Kira and M. Isobe, Chem. Lett., 1996, 473; M. Inoue, M. Sasaki and K. Tachibana, Tetrahedron Lett., 1997, 38, 1611; T. Oka, K. Fujiwara and A. Murai, Tetrahedron Lett., 1997, 38, 8053; M. Inoue, M. Sasaki and K. Tachibana, Angew. Chem., Int. Ed., 1998, 37, 965; M. Sasaki, T. Noguchi and K. Tachibana, Tetrahedron Lett., 1999, 40, 1337.
4. For recent synthetic studies, see: T. Oishi, M. Shoji, K. Maeda, N. Kumahara and M. Hirama, Synlett, 1996, 1165; T. Oishi, K. Maeda and M. Hirama, Chem. Commun., 1997, 1289; T. Oishi, M. Shoji, N. Kumahara and M. Hirama, Chem. Lett., 1997, 845; T. Oishi, Y. Nagumo and M. Hirama, Synlett, 1997, 307; S. Hosokawa and M. Isobe, Synlett, 1996, 351; T. Oka, K. Fujiwara and A. Murai, Tetrahedron, 1996, 37, 1179; E. Alvarez, M. Delgado, M. T. Díaz, L. Hanxing, R. Pérez and J. D. Martín, Tetrahedron Lett., 1996, 37, 2865; J. L. Ravelo, A. Regueiro, E. Rodríguez, J. A. Vera and J. D. Martín, Tetrahedron Lett., 1996, 37, 2869; S. Hosokawa, K. Kira and M. Isobe, Chem. Lett., 1996, 473; M. Inoue, M. Sasaki and K. Tachibana, Tetrahedron Lett., 1997, 38, 1611; T. Oka, K. Fujiwara and A. Murai, Tetrahedron Lett., 1997, 38, 8053; M. Inoue, M. Sasaki and K. Tachibana, Angew. Chem., Int. Ed., 1998, 37, 965; M. Sasaki, T. Noguchi and K. Tachibana, Tetrahedron Lett., 1999, 40, 1337.
5. For recent synthetic studies, see: T. Oishi, M. Shoji, K. Maeda, N. Kumahara and M. Hirama, Synlett, 1996, 1165; T. Oishi, K. Maeda and M. Hirama, Chem. Commun., 1997, 1289; T. Oishi, M. Shoji, N. Kumahara and M. Hirama, Chem. Lett., 1997, 845; T. Oishi, Y. Nagumo and M. Hirama, Synlett, 1997, 307; S. Hosokawa and M. Isobe, Synlett, 1996, 351; T. Oka, K. Fujiwara and A. Murai, Tetrahedron, 1996, 37, 1179; E. Alvarez, M. Delgado, M. T. Díaz, L. Hanxing, R. Pérez and J. D. Martín, Tetrahedron Lett., 1996, 37, 2865; J. L. Ravelo, A. Regueiro, E. Rodríguez, J. A. Vera and J. D. Martín, Tetrahedron Lett., 1996, 37, 2869; S. Hosokawa, K. Kira and M. Isobe, Chem. Lett., 1996, 473; M. Inoue, M. Sasaki and K. Tachibana, Tetrahedron Lett., 1997, 38, 1611; T. Oka, K. Fujiwara and A. Murai, Tetrahedron Lett., 1997, 38, 8053; M. Inoue, M. Sasaki and K. Tachibana, Angew. Chem., Int. Ed., 1998, 37, 965; M. Sasaki, T. Noguchi and K. Tachibana, Tetrahedron Lett., 1999, 40, 1337.
6. For recent synthetic studies, see: T. Oishi, M. Shoji, K. Maeda, N. Kumahara and M. Hirama, Synlett, 1996, 1165; T. Oishi, K. Maeda and M. Hirama, Chem. Commun., 1997, 1289; T. Oishi, M. Shoji, N. Kumahara and M. Hirama, Chem. Lett., 1997, 845; T. Oishi, Y. Nagumo and M. Hirama, Synlett, 1997, 307; S. Hosokawa and M. Isobe, Synlett, 1996, 351; T. Oka, K. Fujiwara and A. Murai, Tetrahedron, 1996, 37, 1179; E. Alvarez, M. Delgado, M. T. Díaz, L. Hanxing, R. Pérez and J. D. Martín, Tetrahedron Lett., 1996, 37, 2865; J. L. Ravelo, A. Regueiro, E. Rodríguez, J. A. Vera and J. D. Martín, Tetrahedron Lett., 1996, 37, 2869; S. Hosokawa, K. Kira and M. Isobe, Chem. Lett., 1996, 473; M. Inoue, M. Sasaki and K. Tachibana, Tetrahedron Lett., 1997, 38, 1611; T. Oka, K. Fujiwara and A. Murai, Tetrahedron Lett., 1997, 38, 8053; M. Inoue, M. Sasaki and K. Tachibana, Angew. Chem., Int. Ed., 1998, 37, 965; M. Sasaki, T. Noguchi and K. Tachibana, Tetrahedron Lett., 1999, 40, 1337.
7. For recent synthetic studies, see: T. Oishi, M. Shoji, K. Maeda, N. Kumahara and M. Hirama, Synlett, 1996, 1165; T. Oishi, K. Maeda and M. Hirama, Chem. Commun., 1997, 1289; T. Oishi, M. Shoji, N. Kumahara and M. Hirama, Chem. Lett., 1997, 845; T. Oishi, Y. Nagumo and M. Hirama, Synlett, 1997, 307; S. Hosokawa and M. Isobe, Synlett, 1996, 351; T. Oka, K. Fujiwara and A. Murai, Tetrahedron, 1996, 37, 1179; E. Alvarez, M. Delgado, M. T. Díaz, L. Hanxing, R. Pérez and J. D. Martín, Tetrahedron Lett., 1996, 37, 2865; J. L. Ravelo, A. Regueiro, E. Rodríguez, J. A. Vera and J. D. Martín, Tetrahedron Lett., 1996, 37, 2869; S. Hosokawa, K. Kira and M. Isobe, Chem. Lett., 1996, 473; M. Inoue, M. Sasaki and K. Tachibana, Tetrahedron Lett., 1997, 38, 1611; T. Oka, K. Fujiwara and A. Murai, Tetrahedron Lett., 1997, 38, 8053; M. Inoue, M. Sasaki and K. Tachibana, Angew. Chem., Int. Ed., 1998, 37, 965; M. Sasaki, T. Noguchi and K. Tachibana, Tetrahedron Lett., 1999, 40, 1337.
8. For recent synthetic studies, see: T. Oishi, M. Shoji, K. Maeda, N. Kumahara and M. Hirama, Synlett, 1996, 1165; T. Oishi, K. Maeda and M. Hirama, Chem. Commun., 1997, 1289; T. Oishi, M. Shoji, N. Kumahara and M. Hirama, Chem. Lett., 1997, 845; T. Oishi, Y. Nagumo and M. Hirama, Synlett, 1997, 307; S. Hosokawa and M. Isobe, Synlett, 1996, 351; T. Oka, K. Fujiwara and A. Murai, Tetrahedron, 1996, 37, 1179; E. Alvarez, M. Delgado, M. T. Díaz, L. Hanxing, R. Pérez and J. D. Martín, Tetrahedron Lett., 1996, 37, 2865; J. L. Ravelo, A. Regueiro, E. Rodríguez, J. A. Vera and J. D. Martín, Tetrahedron Lett., 1996, 37, 2869; S. Hosokawa, K. Kira and M. Isobe, Chem. Lett., 1996, 473; M. Inoue, M. Sasaki and K. Tachibana, Tetrahedron Lett., 1997, 38, 1611; T. Oka, K. Fujiwara and A. Murai, Tetrahedron Lett., 1997, 38, 8053; M. Inoue, M. Sasaki and K. Tachibana, Angew. Chem., Int. Ed., 1998, 37, 965; M. Sasaki, T. Noguchi and K. Tachibana, Tetrahedron Lett., 1999, 40, 1337.
9. For recent synthetic studies, see: T. Oishi, M. Shoji, K. Maeda, N. Kumahara and M. Hirama, Synlett, 1996, 1165; T. Oishi, K. Maeda and M. Hirama, Chem. Commun., 1997, 1289; T. Oishi, M. Shoji, N. Kumahara and M. Hirama, Chem. Lett., 1997, 845; T. Oishi, Y. Nagumo and M. Hirama, Synlett, 1997, 307; S. Hosokawa and M. Isobe, Synlett, 1996, 351; T. Oka, K. Fujiwara and A. Murai, Tetrahedron, 1996, 37, 1179; E. Alvarez, M. Delgado, M. T. Díaz, L. Hanxing, R. Pérez and J. D. Martín, Tetrahedron Lett., 1996, 37, 2865; J. L. Ravelo, A. Regueiro, E. Rodríguez, J. A. Vera and J. D. Martín, Tetrahedron Lett., 1996, 37, 2869; S. Hosokawa, K. Kira and M. Isobe, Chem. Lett., 1996, 473; M. Inoue, M. Sasaki and K. Tachibana, Tetrahedron Lett., 1997, 38, 1611; T. Oka, K. Fujiwara and A. Murai, Tetrahedron Lett., 1997, 38, 8053; M. Inoue, M. Sasaki and K. Tachibana, Angew. Chem., Int. Ed., 1998, 37, 965; M. Sasaki, T. Noguchi and K. Tachibana, Tetrahedron Lett., 1999, 40, 1337.
10. For recent synthetic studies, see: T. Oishi, M. Shoji, K. Maeda, N. Kumahara and M. Hirama, Synlett, 1996, 1165; T. Oishi, K. Maeda and M. Hirama, Chem. Commun., 1997, 1289; T. Oishi, M. Shoji, N. Kumahara and M. Hirama, Chem. Lett., 1997, 845; T. Oishi, Y. Nagumo and M. Hirama, Synlett, 1997, 307; S. Hosokawa and M. Isobe, Synlett, 1996, 351; T. Oka, K. Fujiwara and A. Murai, Tetrahedron, 1996, 37, 1179; E. Alvarez, M. Delgado, M. T. Díaz, L. Hanxing, R. Pérez and J. D. Martín, Tetrahedron Lett., 1996, 37, 2865; J. L. Ravelo, A. Regueiro, E. Rodríguez, J. A. Vera and J. D. Martín, Tetrahedron Lett., 1996, 37, 2869; S. Hosokawa, K. Kira and M. Isobe, Chem. Lett., 1996, 473; M. Inoue, M. Sasaki and K. Tachibana, Tetrahedron Lett., 1997, 38, 1611; T. Oka, K. Fujiwara and A. Murai, Tetrahedron Lett., 1997, 38, 8053; M. Inoue, M. Sasaki and K. Tachibana, Angew. Chem., Int. Ed., 1998, 37, 965; M. Sasaki, T. Noguchi and K. Tachibana, Tetrahedron Lett., 1999, 40, 1337.
11. For recent synthetic studies, see: T. Oishi, M. Shoji, K. Maeda, N. Kumahara and M. Hirama, Synlett, 1996, 1165; T. Oishi, K. Maeda and M. Hirama, Chem. Commun., 1997, 1289; T. Oishi, M. Shoji, N. Kumahara and M. Hirama, Chem. Lett., 1997, 845; T. Oishi, Y. Nagumo and M. Hirama, Synlett, 1997, 307; S. Hosokawa and M. Isobe, Synlett, 1996, 351; T. Oka, K. Fujiwara and A. Murai, Tetrahedron, 1996, 37, 1179; E. Alvarez, M. Delgado, M. T. Díaz, L. Hanxing, R. Pérez and J. D. Martín, Tetrahedron Lett., 1996, 37, 2865; J. L. Ravelo, A. Regueiro, E. Rodríguez, J. A. Vera and J. D. Martín, Tetrahedron Lett., 1996, 37, 2869; S. Hosokawa, K. Kira and M. Isobe, Chem. Lett., 1996, 473; M. Inoue, M. Sasaki and K. Tachibana, Tetrahedron Lett., 1997, 38, 1611; T. Oka, K. Fujiwara and A. Murai, Tetrahedron Lett., 1997, 38, 8053; M. Inoue, M. Sasaki and K. Tachibana, Angew. Chem., Int. Ed., 1998, 37, 965; M. Sasaki, T. Noguchi and K. Tachibana, Tetrahedron Lett., 1999, 40, 1337.
12. For recent synthetic studies, see: T. Oishi, M. Shoji, K. Maeda, N. Kumahara and M. Hirama, Synlett, 1996, 1165; T. Oishi, K. Maeda and M. Hirama, Chem. Commun., 1997, 1289; T. Oishi, M. Shoji, N. Kumahara and M. Hirama, Chem. Lett., 1997, 845; T. Oishi, Y. Nagumo and M. Hirama, Synlett, 1997, 307; S. Hosokawa and M. Isobe, Synlett, 1996, 351; T. Oka, K. Fujiwara and A. Murai, Tetrahedron, 1996, 37, 1179; E. Alvarez, M. Delgado, M. T. Díaz, L. Hanxing, R. Pérez and J. D. Martín, Tetrahedron Lett., 1996, 37, 2865; J. L. Ravelo, A. Regueiro, E. Rodríguez, J. A. Vera and J. D. Martín, Tetrahedron Lett., 1996, 37, 2869; S. Hosokawa, K. Kira and M. Isobe, Chem. Lett., 1996, 473; M. Inoue, M. Sasaki and K. Tachibana, Tetrahedron Lett., 1997, 38, 1611; T. Oka, K. Fujiwara and A. Murai, Tetrahedron Lett., 1997, 38, 8053; M. Inoue, M. Sasaki and K. Tachibana, Angew. Chem., Int. Ed., 1998, 37, 965; M. Sasaki, T. Noguchi and K. Tachibana, Tetrahedron Lett., 1999, 40, 1337.
13. For recent synthetic studies, see: T. Oishi, M. Shoji, K. Maeda, N. Kumahara and M. Hirama, Synlett, 1996, 1165; T. Oishi, K. Maeda and M. Hirama, Chem. Commun., 1997, 1289; T. Oishi, M. Shoji, N. Kumahara and M. Hirama, Chem. Lett., 1997, 845; T. Oishi, Y. Nagumo and M. Hirama, Synlett, 1997, 307; S. Hosokawa and M. Isobe, Synlett, 1996, 351; T. Oka, K. Fujiwara and A. Murai, Tetrahedron, 1996, 37, 1179; E. Alvarez, M. Delgado, M. T. Díaz, L. Hanxing, R. Pérez and J. D. Martín, Tetrahedron Lett., 1996, 37, 2865; J. L. Ravelo, A. Regueiro, E. Rodríguez, J. A. Vera and J. D. Martín, Tetrahedron Lett., 1996, 37, 2869; S. Hosokawa, K. Kira and M. Isobe, Chem. Lett., 1996, 473; M. Inoue, M. Sasaki and K. Tachibana, Tetrahedron Lett., 1997, 38, 1611; T. Oka, K. Fujiwara and A. Murai, Tetrahedron Lett., 1997, 38, 8053; M. Inoue, M. Sasaki and K. Tachibana, Angew. Chem., Int. Ed., 1998, 37, 965; M. Sasaki, T. Noguchi and K. Tachibana, Tetrahedron Lett., 1999, 40, 1337.
14. For recent synthetic studies, see: T. Oishi, M. Shoji, K. Maeda, N. Kumahara and M. Hirama, Synlett, 1996, 1165; T. Oishi, K. Maeda and M. Hirama, Chem. Commun., 1997, 1289; T. Oishi, M. Shoji, N. Kumahara and M. Hirama, Chem. Lett., 1997, 845; T. Oishi, Y. Nagumo and M. Hirama, Synlett, 1997, 307; S. Hosokawa and M. Isobe, Synlett, 1996, 351; T. Oka, K. Fujiwara and A. Murai, Tetrahedron, 1996, 37, 1179; E. Alvarez, M. Delgado, M. T. Díaz, L. Hanxing, R. Pérez and J. D. Martín, Tetrahedron Lett., 1996, 37, 2865; J. L. Ravelo, A. Regueiro, E. Rodríguez, J. A. Vera and J. D. Martín, Tetrahedron Lett., 1996, 37, 2869; S. Hosokawa, K. Kira and M. Isobe, Chem. Lett., 1996, 473; M. Inoue, M. Sasaki and K. Tachibana, Tetrahedron Lett., 1997, 38, 1611; T. Oka, K. Fujiwara and A. Murai, Tetrahedron Lett., 1997, 38, 8053; M. Inoue, M. Sasaki and K. Tachibana, Angew. Chem., Int. Ed., 1998, 37, 965; M. Sasaki, T. Noguchi and K. Tachibana, Tetrahedron Lett., 1999, 40, 1337.
15. For recent synthetic studies, see: T. Oishi, M. Shoji, K. Maeda, N. Kumahara and M. Hirama, Synlett, 1996, 1165; T. Oishi, K. Maeda and M. Hirama, Chem. Commun., 1997, 1289; T. Oishi, M. Shoji, N. Kumahara and M. Hirama, Chem. Lett., 1997, 845; T. Oishi, Y. Nagumo and M. Hirama, Synlett, 1997, 307; S. Hosokawa and M. Isobe, Synlett, 1996, 351; T. Oka, K. Fujiwara and A. Murai, Tetrahedron, 1996, 37, 1179; E. Alvarez, M. Delgado, M. T. Díaz, L. Hanxing, R. Pérez and J. D. Martín, Tetrahedron Lett., 1996, 37, 2865; J. L. Ravelo, A. Regueiro, E. Rodríguez, J. A. Vera and J. D. Martín, Tetrahedron Lett., 1996, 37, 2869; S. Hosokawa, K. Kira and M. Isobe, Chem. Lett., 1996, 473; M. Inoue, M. Sasaki and K. Tachibana, Tetrahedron Lett., 1997, 38, 1611; T. Oka, K. Fujiwara and A. Murai, Tetrahedron Lett., 1997, 38, 8053; M. Inoue, M. Sasaki and K. Tachibana, Angew. Chem., Int. Ed., 1998, 37, 965; M. Sasaki, T. Noguchi and K. Tachibana, Tetrahedron Lett., 1999, 40, 1337.
16. T. Oishi, Y. Nagumo and M. Hirama, Chem. Commun., 1998, 1041.
17. C. H. Marzabadi and C. D. Spilling, J. Org. Chem., 1993, 58, 3761.
18. P. Schwab. R. H. Grubbs and J. W. Ziller, J. Am. Chem. Soc., 1996, 118, 100.
19. M. Delgago and J. D. Martín, Tetrahedron Lett., 1997, 38, 6299.
20. R. Johansson and B. Samuelsson, J. Chem. Soc., Chem. Commun., 1984, 201.
21. I. Kadota, A. Ohno, Y. Matsukawa and Y. Yamamoto, Tetrahedron Lett., 1998, 39, 6373.
22. 2 gave a remarkably higher yield of the reduction product; 0-70% yield in the case of hemiacetal under the same reduction conditions. Also see ref. 3.
23. D. L. Lewis, J. K. Cha and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 4976.
24. 2Ph), 5.64 (1H, dt, J 13.0, 2.3, H18), 5.77 (1H, dddd, J 11.8, 5.1, 3.5, 2.8, H7), 5.83 (1H, dt, J 13.0, 2.3, H17), 5.87 (1H, ddt, J 11.8, 5.7, 2.8, H6), 7.23-7.43 (17H, m, Ph), 7.52-7.56 (4H, m, Ph), 7.59-7.66 (4H, m, Ph).