The stereochemical assignment and conformational analysis of the V/W-ring juncture of maitotoxin

Journal of the American Chemical Society

Volumn 119, Issue 34, 1997, Pages 7928-7937

  Cook, Laura R ^a   Oinuma, Hitoshi ^a   Semones, Marcus A ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MAITOTOXIN;

ARTICLE; CHEMICAL BOND; CONFORMATION; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS; TOXIN ANALYSIS;

EID: 0030865705     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971259t     Document Type: Article

References (44)

1. Yasumoto, T.; Bagnis, R.; Vernoux, J. P. Bull. Jpn. Soc. Sci. Fish. 1976, 42, 359-365.
2. (a) Yasumoto, T.; Nakajima, I.; Oshima, Y.; Bagnis, R. In Toxic Dinoflagellate Blooms; Taylor, D. L., Seliger, H., Eds.; Elsevier: North Holland, 1979; pp 65-70.
3. (b) Yokoyama, A.; Murata, M.; Oshima, Y.; Iwashita, T.; Yasumoto, T. J. Biochem. 1988, 104, 184-187.
4. (c) Takahashi, M.; Ohizumi, Y.; Yasumoto, T. J. Biol. Chem. 1982, 257, 7287-7289.
5. Murata, M.; Naoki, H.; Iwashita, T.; Matsunaga, S.; Sasaki, M.; Yokoyama, A.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 2060-2062.
6. Murata, M.; Naoki, H.; Matsunaga, S.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1994, 116, 7098-7107.
7. (a) Sasaki, M.; Nonomura, T.; Murata, M.; Tachibana, K. Tetrahedron Lett. 1994, 35, 5023-5026.
8. (b) Sasaki, M.; Nonomura, T.; Murata, M.; Tachibana, K. Tetrahedron Lett. 1995, 36, 9007-9010.
9. (c) Sasaki, M.; Matsumori, N.; Murata, M.; Tachibana, K.; Yasumoto, T. Tetrahedron Lett. 1995, 36, 9011-9014.
10. (d) Matsumori, N.; Nonomura, T.; Sasaki, M.; Murata, M.; Tachibana, K.; Satake, M.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 1269-1272.
11. (e) Sasaki, M.; Matsumori, N.; Maruyama, T.; Nonomura, T.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1672-1675.
12. (f) Nonomura, T.; Sasaki, M.; Matsumori, N.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1675-1678.
13. Zheng, W.; DeMattei, J. A.; Wu, J.-P.; Duan, J. J.-W.; Cook, L. R.; Oinuma, H.; Kishi, Y. J. Am. Chem. Soc. 1996, 118, 7946-7968.
14. The absolute stereochemistry of MTX has been assigned: (a) ref 5f. (b) Oinuma, H.; Kim, H.; Kishi, Y. Unpublished work. Also, see the note added in the proof of ref 6.
15. The absolute stereochemistry of MTX has been assigned: (a) ref 5f. (b) Oinuma, H.; Kim, H.; Kishi, Y. Unpublished work. Also, see the note added in the proof of ref 6.
16. 2- and the Me-model series we opted to study the stereochemical assignment and conformational analysis of the V/W-ring juncture with the antipode of MTX.
17. The synthesis of these two models is described in detail in the Supporting Information, and the results of the NMR spectroscopic study were added to the 1996 publication as the note added in the proof. See ref 6.
18. 2-A was established by the crystal structure of its bis-3′,5′-dinitrobenzoate derivative as shown below. The DNBz groups were removed from the representation for clarity. (Equation Presented)
19. There are numerous examples known for this type of reduction with ionic or radical conditions. For example, see: (a) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978. (b) Nicolaou, K. C.; Duggan, M. E.; Hwang, C. K. J. Am. Chem. Soc. 1986, 108, 2468-2469.
20. There are numerous examples known for this type of reduction with ionic or radical conditions. For example, see: (a) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978. (b) Nicolaou, K. C.; Duggan, M. E.; Hwang, C. K. J. Am. Chem. Soc. 1986, 108, 2468-2469.
21. (a) Jin, H.; Uenishi, J.-i.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644-5646.
22. (b) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281-5284.
23. (a) Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517-4552.
24. (b) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 6676-6682.
25. Kang, S. H.; Hwang, T. S.; Kim, W. J.; Lim, J. K. Tetrahedron Lett. 1990, 31, 5917-5920.
26. Clive, D. L. J.; Chittattu, G. J.; Farina, V.; Kiel, W. A.; Menchen, S. M.; Russell, C. G.; Singh, A.; Wong, C. K.; Curtis, N. J. J. Am. Chem. Soc. 1980, 102, 4438-4447.
27. The X-ray crystal structure of 4 is shown below. (Equation Presented)
28. (a) Mancuso, A. J.; Swern, D. Synthesis 1981, 165-185.
29. (b) Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651-1660.
30. (c) Huang, S. L.; Omura, K.; Swern, D. Synthesis 1978, 297-299.
31. 2-Methyl-5-hexen-2-ol is commercially available, but for this work it was prepared in two steps from 4-pentenoic acid: 1. esterification with methanol in the presence of CSA and 2. methyl magnesium iodide addition , to the methyl ester.
32. (a) Classon, B.; Garegg, P. J.; Samuelsson, B. Acta. Chem. Scand. Ser. B. 1984, B38, 419-422.
33. (b) Johansson, R.; Samuelsson, B. J. Chem. Soc., Perkin Trans. I 1984, 2371-2374.
34. Based on the large H.96-H.95 coupling constant, it was demonstrated that both H.96 and H.95 must be axial on the pyran ring.
35. The stereochemistry at the carbinol center of 9 and 10 was not assigned.
36. There are several cases known where the Ni(II)/Cr(II)-mediated coupling reactions are highly stereoselective or even stereospecific. For example, see: (a) Ref 12a. (b) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. (c) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.; Jung, S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992, 114, 3162-3164.
37. There are several cases known where the Ni(II)/Cr(II)-mediated coupling reactions are highly stereoselective or even stereospecific. For example, see: (a) Ref 12a. (b) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. (c) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.; Jung, S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992, 114, 3162-3164.
38. There are several cases known where the Ni(II)/Cr(II)-mediated coupling reactions are highly stereoselective or even stereospecific. For example, see: (a) Ref 12a. (b) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737. (c) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.; Jung, S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992, 114, 3162-3164.
39. 2-A.
40. 6 are included in the supporting information.
41. Chloroform and water were the only solvent choices for MM3 calculations.
42. (a) Bal, B. S.; Childers, W. E., Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2091-2096.
43. (b) Hillis, L. R.; Ronald, R. C., Jr. J. Org. Chem. 1985, 50, 470-473.
44. Stamos, D. P. Ph.D. Thesis, Harvard University, 1997.