Convergent synthesis of an HIJK ring model of ciguatoxin via Suzuki cross-coupling reaction

Tetrahedron Letters

Volumn 41, Issue 9, 2000, Pages 1425-1428

  Sasaki, Makoto ^a   Noguchi, Katsuhiko ^a   Fuwa, Haruhiko ^a   Tachibana, Kazuo ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Coupling reactions; Polyethers; Suzuki reactions; Toxins

Indexed keywords

CIGUATOXIN; PALLADIUM; POLYETHER DERIVATIVE; TOXIN;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

LATEOLABRAX JAPONICUS;

EID: 0034716551     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02307-2     Document Type: Article

References (42)

1. For recent reviews on ciguatoxins and related marine toxins, see: (a) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897.
2. (b) Scheuer, P. J. Tetrahedron 1994, 50, 3.
3. For recent reviews on polyether synthesis, see: (a) Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martín, J. D. Chem. Rev. 1995, 95, 1953.
4. (b) Mori, Y. Chem. Eur. J. 1997, 3, 849.
5. For recent synthetic work from other laboratories, see: (a) Oka, T.; Fujiwara, K.; Murai, A. Tetrahedron 1996, 52, 12091.
6. (b) Oishi, T.; Shoji, M.; Maeda, K.; Kumahara, N.; Hirama, M. Synlett 1996, 1165.
7. (c) Alvarez, E.; Delgado, M.; Díaz, M. T.; Hanxing, L.; Pérez, R.; Martín, J. D. Tetrahedron Lett. 1996, 37, 2865.
8. (d) Isobe, M.; Hosokawa, S.; Kira, K. Chem. Lett. 1996, 473.
9. (e) Atsuta, H.; Fujiwara, K.; Murai, A. Synlett 1997, 307.
10. (f) Oishi, T.; Maeda, K.; Hirama, M. Chem. Commun. 1997, 1289.
11. (g) Oguri, H.; Hishiyama, S.; Sato, O.; Oishi, T.; Hirama, M.; Murata, M.; Yasumoto, T.; Harada, N. Tetrahedron 1997, 53, 3057.
12. (h) Oishi, T.; Shoji, M.; Kumahara, N.; Hirama, M. Chem. Lett. 1997, 845.
13. (i) Oka, T.; Fujiwara, K.; Murai, A. Tetrahedron Lett. 1997, 38, 8053.
14. (j) Ami, E.; Kishimoto, H.; Ohrui, H.; Meguro, H. Biosci. Biotechnol. Biochem. 1997, 61, 2019.
15. (k) Oka, T.; Murai, A. Tetrahedron 1998, 54, 1.
16. (l) Oka, T.; Fujiwara, K.; Murai, A. Tetrahedron 1998, 54, 21.
17. (m) Oishi, T.; Nagumo, Y.; Hirama, M. Chem. Commun. 1998, 1359.
18. (n) Isobe, M.; Nishizawa, R.; Hosokawa, S.; Nishikawa, T. Chem. Commun. 1998, 2665.
19. (o) Hosokawa, S.; Isobe, M. J. Org. Chem. 1999, 64, 37.
20. (p) Saeeng, R.; Isobe, M. Tetrahedron Lett. 1999, 40, 1911.
21. (q) Oguri, H.; Sasaki, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1999, 40, 5405.
22. (r) Maeda, K.; Oishi, T.; Oguri, H.; Hirama, M. Chem. Commun. 1999, 1063.
23. (s) Oguri, H.; Tanaka, S.; Hishiyama, S.; Oishi, T.; Hirama, N.; Tumuraya, T.; Tomioka, Y.; Mizugaki, M. Synthesis 1999, 1431 and references cited therein.
24. For our synthetic studies on ciguatoxins, see: (a) Sasaki, M.; Hasegawa, A.; Tachibana, K. Tetrahedron Lett. 1993, 34, 8489.
25. (b) Sasaki, M.; Inoue, M.; Tachibana, K. J. Org. Chem. 1994, 59, 715.
26. (c) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611.
27. (d) Inoue, M.; Sasaki, M.; Tachibana, K. Angew. Chem., Int. Ed. Engl. 1998, 37, 965.
28. (e) Sasaki, M.; Inoue, M.; Noguchi, T.; Takeichi, A.; Tachibana, K. Tetrahedron Lett. 1998, 39, 2783.
29. (f) Sasaki, M.; Fuwa, H.; Inoue, M.; Tachibana, K. Tetrahedron Lett. 1998, 39, 9027.
30. (g) Sasaki, M.; Noguchi, T.; Tachibana, K. Tetrahedron Lett. 1999, 40, 1337.
31. (h) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron 1999, 55, 10949.
32. (i) Sasaki, M.; Fuwa, H.; Ishikawa, M.; Tachibana, K. Org. Lett. 1999, 1, 1075.
33. (j) Sasaki, M.; Inoue, M.; Takamatsu, K. J. Org. Chem. 1999, 64, 9399.
34. (k) Inoue, M.; Sasaki, M.; Tachibana, K. J. Org. Chem. 1999, 64, 9416.
35. Nicolaou, K. C.; McGarry, D. G.; Somers, P. K.; Kim, B. H.; Ogilvie, W. W.; Yiannikouros, G.; Prasad, C. V. C.; Veale, C. A.; Hark, R. P. J. Am. Chem. Soc. 1990, 112, 6263.
36. Nicolaou, K. C.; Shi, G.-Q.; Gunzner, J. L.; Gärtner, G. P.; Yang, Z. J. Am. Chem. Soc. 1997, 119, 5467.
37. Kadota, I.; Ohno, A.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1998, 39, 7373.
38. Hydroboration of 3 with 9-BBN followed by oxidative workup stereoselectively gave alcohol 5 in 75% yield.
39. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
40. The carbon numbering corresponding to that of ciguatoxin was used throughout this paper.
41. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011.
42. +]: 463.2308; found: 463.2309.