A Unified Procedure for Diastereo- and Enantiocontrolled Construction of Compactin Lactone and Calcitriol Enyne

Synlett

Volumn 1997, Issue 9, 1997, Pages 1111-1113

  Oizumi, Mitsuru ^a   Takahashi, Michiyasu ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002698572     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1550     Document Type: Article

References (34)

1. Endo, A.; Kuroda, M.; Tsujita, Y. J. Antibiot. 1976, 29, 1346. Brown, A. G.; Smale, T. C.; King, T. J.; Hasenkamp, R.; Thompson, R. H. J. Chem. Soc., Perkin Trans. 1 1976, 1165.
2. Endo, A.; Kuroda, M.; Tsujita, Y. J. Antibiot. 1976, 29, 1346. Brown, A. G.; Smale, T. C.; King, T. J.; Hasenkamp, R.; Thompson, R. H. J. Chem. Soc., Perkin Trans. 1 1976, 1165.
3. Okamura, W. H.; Midland, M. M.; Hammond, M. W.; Abd. Rahman, N.; Dormanen, M. C.; Nemere, I.; Norman, A. W. J. Steroid Biochem. Molec. Biol. 1995, 53, 603.
4. Grundy, S. M. New Engl. J. Med. 1988, 319, 24. Brown, M. S.; Goldstein, J. L. Science 1986, 232, 34. Henwood, J. M.; Heel, R. C. Drugs 1988, 36, 429.
5. Grundy, S. M. New Engl. J. Med. 1988, 319, 24. Brown, M. S.; Goldstein, J. L. Science 1986, 232, 34. Henwood, J. M.; Heel, R. C. Drugs 1988, 36, 429.
6. Grundy, S. M. New Engl. J. Med. 1988, 319, 24. Brown, M. S.; Goldstein, J. L. Science 1986, 232, 34. Henwood, J. M.; Heel, R. C. Drugs 1988, 36, 429.
7. A pertinent review, see: Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocrine Rev. 1995, 16, 200.
8. A recent review for the synthesis of compactin, see: Yadav, V. K.; Kopoor, K. K. Indian J. Chem., Sect B. 1996, 35B, 1125. See also: Bauer, T.; Chapuis, C.; Jezewski, A.; Kozak, J.; Jurczak, J. Tetrahedron: Asymmetry 1996, 7, 1391.
9. A recent review for the synthesis of compactin, see: Yadav, V. K.; Kopoor, K. K. Indian J. Chem., Sect B. 1996, 35B, 1125. See also: Bauer, T.; Chapuis, C.; Jezewski, A.; Kozak, J.; Jurczak, J. Tetrahedron: Asymmetry 1996, 7, 1391.
10. Recent reviews for the synthesis of vitamin D, see: Dai, H.; Posner, G. H. Synthesis 1994, 1383. Zhu, G. -D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877.
11. Recent reviews for the synthesis of vitamin D, see: Dai, H.; Posner, G. H. Synthesis 1994, 1383. Zhu, G. -D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877.
12. Takano, S.; Shimazaki, Y.; Sekiguchi, Y.; Ogasawara, K. Synthesis 1989, 539.
13. Trost, B. M.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1924. Trost, B. M.; Dumas, J.; Villa, M. J. Am. Chem. Soc. 1992, 114, 9836.
14. Trost, B. M.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1924. Trost, B. M.; Dumas, J.; Villa, M. J. Am. Chem. Soc. 1992, 114, 9836.
15. Tazumi, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1994, 1903.
16. Trost, B. M.; Hanson, P. R. Tetrahedron Lett. 1994, 35, 8119.
17. Moriarty, R. M.; Kim, J.; Brumer III, H. Tetrahedron Lett. 1995, 36, 51.
18. Vrielynck, S.; Vandewalle, M.; Garcia, A. M.; Mascarenas, J. L.; Mourino, A. Tetrahedron Lett. 1995, 36, 9023.
19. Baggiolini, E. G.; Iacobelli, J. A.; Hennessy, B. M.; Uskokovic, M. R. J. Am. Chem. Soc. 1982, 104, 2945. Baggiolini, E. G.; Iacobelli, J. A.; Hennessy, B. M.; Batcho, A. D.; Sereno, J. F.; Uskokovic, M. R. J. Org. Chem. 1986, 51, 3098.
20. Baggiolini, E. G.; Iacobelli, J. A.; Hennessy, B. M.; Uskokovic, M. R. J. Am. Chem. Soc. 1982, 104, 2945. Baggiolini, E. G.; Iacobelli, J. A.; Hennessy, B. M.; Batcho, A. D.; Sereno, J. F.; Uskokovic, M. R. J. Org. Chem. 1986, 51, 3098.
21. Optically pure epichlorohydrin is commercially available in both enantiomeric forms from DAISO Corporation, Osaka, Japan.
22. Chiral epichlorohydrin has been used for the construction of a non-natural HMG Co-A reductase inhibitor NK-104; Takano, S.; Kamikubo, T.; Sugihara, T.; Suzuki, M.; Ogasawara, K. Tetrahedron: Asymmetry 1993, 4, 201.
23. Chiral epichlorohydrin has been used for the construction of the A-ring moiety of calcitriol: (a) ref. 9. (b) Hatakeyama, S.; Irie, H.; Shintani, T.; Noguchi, Y.; Yamada, H.; Nishizawa, M. Tetrahedron 1994, 50, 13369.
24. Takano, S.; Sekiguchi, Y.; Setoh, M.; Yoshimitsu, T.; Inomata, K.; Takahashi, M.; Ogasawara, K. Heterocycles 1990, 31, 1715.
25. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391.
26. Takano, S.; Shimazaki, Y.; Moriya, M.; Ogasawara, K. Chem. Lett. 1990, 1177.
27. Weihe, G. R.; McMorris, T. C. J. Org. Chem. 1978, 43, 3942.
28. Miyashita, M.; Suzuki, T.; Yoshikoshi, A. Tetrahedron Lett. 1987, 28, 4293. Miyashita, M.; Hoshino, M.; Suzuki, T.; Yoshikoshi, A. Chem. Lett. 1988, 507.
29. Miyashita, M.; Suzuki, T.; Yoshikoshi, A. Tetrahedron Lett. 1987, 28, 4293. Miyashita, M.; Hoshino, M.; Suzuki, T.; Yoshikoshi, A. Chem. Lett. 1988, 507.
30. 4).
31. Nakagawa, I.; Hata, T. Tetrahedron Lett. 1975, 1409. Nakagawa, I.; Aki, K.; Hata, T. J. Chem. Soc., Perkin Trans. 1 1983, 1315.
32. Nakagawa, I.; Hata, T. Tetrahedron Lett. 1975, 1409. Nakagawa, I.; Aki, K.; Hata, T. J. Chem. Soc., Perkin Trans. 1 1983, 1315.
33. Cf. Takano, S.; Sekiguchi, Y.; Sato, N.; Ogasawara, K. Synthesis 1987, 139.
34. Entwistle, I. D.; Johnstone, R. A. W. J. Chem. Soc., Chem. Commun. 1965, 29.