An olefin metathesis based strategy for the construction of the JKL, OPQ, and UVW ring systems of maitotoxin

Journal of the American Chemical Society

Volumn 118, Issue 42, 1996, Pages 10335-10336

  Nicolaou, K C ^a   Postema, M H D ^a   Yue, E W ^a   Nadin, A ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

MAITOTOXIN;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029957616     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962862z     Document Type: Article

References (26)

1. 2 absolute stereochemistry and to that of the reported fragments OPQ (14), UVW (23), and JKL (29): (a) Sasaki, M.; Matsumori, N.; Maruyama, T.; Nonomura, T.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem. 1996, 108, 1782. Nonomura, T.; Sasaki, M.; Matsumori, N.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem. 1996, 108, 1786. (b) 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. We thank Professor Y. Kishi for a preprint of this article.
2. 2 absolute stereochemistry and to that of the reported fragments OPQ (14), UVW (23), and JKL (29): (a) Sasaki, M.; Matsumori, N.; Maruyama, T.; Nonomura, T.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem. 1996, 108, 1782. Nonomura, T.; Sasaki, M.; Matsumori, N.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem. 1996, 108, 1786. (b) 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. We thank Professor Y. Kishi for a preprint of this article.
3. 2 absolute stereochemistry and to that of the reported fragments OPQ (14), UVW (23), and JKL (29): (a) Sasaki, M.; Matsumori, N.; Maruyama, T.; Nonomura, T.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem. 1996, 108, 1782. Nonomura, T.; Sasaki, M.; Matsumori, N.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem. 1996, 108, 1786. (b) 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. We thank Professor Y. Kishi for a preprint of this article.
4. (a) Murata, M.; Naoki, H.; Matsunaga, S.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1994, 116, 7098.
5. (b) Sasaki, M.; Nonomura, T.; Murata, M.; Tachibana, K. Tetrahedron Lett. 1995, 36, 9007.
6. (c) Sasaki, M.; Nonomura, T.; Murata, M.; Tachibana, K.; Yasumoto, T. Tetrahedron Lett. 1995, 36, 9011.
7. (d) Sasaki, M.; Nonomura, T.; Murata, M.; Tachibana, K. Tetrahedron Lett. 1994, 35, 5023.
8. Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773.
9. (b) Lee, M. S.; Repeta, D. J.; Nakanishi, K.; Zagorski, M. G. J. Am. Chem. Soc. 1986, 108, 7855.
10. (a) Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029.
11. (b) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
12. (c) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634.
13. Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565.
14. Compounds 2, 3. 24, and 25 were synthesized from D-glucal as described in the Supporting Information.
15. All new compounds exhibited satisfactory spectral and exact mass data. Yields refer to spectroscopically and chromatographically homogeneous materials. All compounds are optically pure.
16. Stereochemical assignments were made by 2-D NMR spectroscopy on the intermediates or the corresponding acetates.
17. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483 and references cited therein.
18. Overreduction of lactol 7 to a triol was a major side reaction.
19. Compounds 10, 18, and 19 were synthesized from 1,4-butanediol as described in the Supporting Information.
20. Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392.
21. Klauss, K.; Bestian, H. Justus Liebigs Ann. Chem. 1962, 654, 8.
22. 4a,5
23. For a recent review on this topic, see: Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martin, D. D. Chem. Rev. 1995, 95, 1953.
24. For a palladium-mediated approach to these systems, see: Nicolaou, K. C.; Sato, M.; Miller, N. D.; Gunzner, J. L.; Renaud, J.; Untersteller, E. Angew. Chem.. Int. Ed. Engl. 1996, 35, 889.
25. For reviews, see: (a) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 588. (b) Nicolaou, K. C. Aldrichimica Acta 1993, 26, 62.
26. For reviews, see: (a) Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 588. (b) Nicolaou, K. C. Aldrichimica Acta 1993, 26, 62.