Total synthesis of gambierol

Organic Letters

Volumn 4, Issue 17, 2002, Pages 2981-2984

  Fuwa, Haruhiko ^a   Sasaki, Makoto ^b   Satake, Masayuki ^b   Tachibana, Kazuo ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CIGUATOXIN; ETHER DERIVATIVE; GAMBIEROL; MARINE TOXIN; PALLADIUM; POLYCYCLIC HYDROCARBON; POLYENE; VINYL BROMIDE; VINYL DERIVATIVE;

ANIMAL; ARTICLE; CHEMISTRY; DINOFLAGELLATE; STEREOISOMERISM; SYNTHESIS;

ANIMALS; CIGUATOXINS; DINOFLAGELLIDA; ETHERS, CYCLIC; MARINE TOXINS; PALLADIUM; POLYCYCLIC COMPOUNDS; POLYENES; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 0001352339     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026394b     Document Type: Article

References (47)

1. For reviews on ciguatoxins and related marine polycyclic ethers, see: (a) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897-1909.
2. (b) Scheuer, P. J. Tetrahedron 1994, 50, 3-18.
3. (c) Murata, M.; Yasumoto, T. Nat. Prod. Rep. 2000. 293-314.
4. (d) Yasumoto, T. Chem. Rec. 2001, 3, 228-242.
5. For reviews, see: (a) Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martín, J. D. Chem. Rev. 1995, 95, 1953-1980.
6. (b) Mori, Y. Chem. Eur. J. 1997, 3, 849-852.
7. Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362.
8. Morohashi, A.; Satake, M.; Yasumoto, T. Tetrahedron Lett. 1998, 39, 97-100.
9. (a) Murata, M.; Legrand, A.-M.; Ishibashi, Y.; Yasumoto, T. J. Am. Chem. Soc. 1989, 112, 8929-8931.
10. (b) Murata, M.; Legrand, A.-M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386.
11. (c) Satake, M.; Morohashi, A.; Oguri, H.; Oishi, T.; Hirama, M.; Harada, N.; Yasumoto, T. J. Am. Chem. Soc. 1997, 119, 11325-11326.
12. (d) Yasumoto, T.; Igarashi, T.; Legrand, A.-M.; Cruchet, P.; Chinain, M.; Fujita, T.; Naoki, H. J. Am. Chem. Soc. 2000, 122, 4988-4989 and references therein.
13. (a) Fuwa, H.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 2000, 41, 8371-8375.
14. (b) Fuwa, H.; Sasaki, M.; Tachibana, K. Tetrahedron 2001, 57, 3019-3033.
15. (c) Fuwa, H.; Sasaki, M.; Tachibana, K. Org. Lett. 2001, 3, 3549-3552.
16. (a) Kadota, I.; Park, C-H.; Ohtaka, M.; Oguro, N.; Yamamoto, Y. Tetrahedron Lett. 1998, 39, 6365-6368.
17. (b) Kadota, I.; Kadowaki, C.; Yoshida, N.; Yamamoto, Y. Tetrahedron Lett. 1998, 39, 6369-6372.
18. (c) Kadota, I.; Ohno, A.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1998, 39, 6373-6376.
19. (d) Kadowaki, C.; Chan, P. W. H.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 5769-5772.
20. (e) Kadota, I.; Takamura, H.; Sato, K.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 4729-4731.
21. (f) Kadota, I.; Ohno, A.; Matsuda, K.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 6702-6703.
22. (g) Sakamoto, Y.; Matsuo, G.; Matsukura, H.; Nakata, T. Org. Lett. 2001, 3, 2749-2752.
23. (h) Kadota, I.; Park, C.-H.; Sato, K.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6195-6198.
24. (i) Kadota, I.; Kadowaki, C.; Takamura, H.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6199-6202.
25. (j) Cox, J. M.; Rainier, J. D. Org. Lett. 2001, 3, 2919-2922.
26. (k) Kadota, I.; Kadowaki, C.; Park, C-H.; Yakamura, H.; Sato, K.; Chan, P. W. H.; Thorand, S.; Yamamoto, Y. Tetrahedron 2002, 58, 1799-1816.
27. (l) Kadota, I.; Ohno, A.; Matsuda, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 3562-3566.
28. (m) Kadota, I.; Takamura, H.; Sato, K.; Yamamoto, Y. J. Org. Chem. 2002, 67, 3494-3498.
29. The corresponding vinyl iodide was too unstable to be used.
30. (a) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221-10222.
31. (b) Matsukawa, Y.; Asao, N.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 3779-3790.
32. A mixed solvent system of 1:1 THF/DMSO was used in the present study due to the low solubility of vinyl stannane 4 in DMSO.
33. In the absence of copper(I) salt, the yield of Stille product 5 was very low.
34. Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748-2749.
35. Han, X.; Stolz, B. M.; Corey, E. J. J. Am. Chem. Soc. 1999, 121 7600-7605.
36. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639-666.
37. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011-1013.
38. Feng, F.; Murai, A. Chem. Lett. 1992, 1587-1590.
39. (a) Freeman, P. K.; Hutchinson, L. L. J. Org. Chem. 1980, 45, 1924-1930.
40. (b) Ireland, R. E.; Smith, M. G. J. Am. Chem. Soc. 1988, 110, 854-860.
41. Corey, E. J.; Fuchs, P. J. Tetrahedron Lett. 1972, 36, 3769-3772.
42. (a) Uenishi, J.; Kawahama, R.; Shiga, Y.; Yonemitsu, O.; Tsuji, J. Tetrahedron Lett. 1996, 37, 6759-6752.
43. (b) Uenishi, J.; Kawahama, R.; Yonemitsu, O.; Tsuji, J. J. Org. Chem. 1996, 61, 5716-5717.
44. (c) Uenishi, J.; Kawahama, R.; Yonemitsu, O.; Tsuji, J. J. Org. Chem. 1998, 63, 8965-8975.
45. 1H NMR analysis of the purified mixture.
46. (a) Noyori, R.; Nishida, I.; Sakata, J.; Nishizawa, M. J. Am. Chem. Soc. 1980, 102, 1223-1225.
47. (b) Scheidt, K. A.; Chen, H.; Follows, B. C.; Chemler, A. R.; Coffey, D. S.; Roush, W. R. J. Org. Chem. 1998, 63, 6436-6437.