Asymmetric synthesis of benzylic quaternary carbon center via an enzymatic reaction

Heterocycles

Volumn 43, Issue 5, 1996, Pages 1031-1047

  Shiotani, Shunsaku ^a   Okada, Hirohiko ^a   Nakamata, Kumiko ^a   Yamamoto, Takako ^a   Sekino, Fumie ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

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[No Author keywords available]

Indexed keywords

EID: 0000118162     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-96-7421     Document Type: Article

References (23)

1. A part of this work has been presented in a preliminary form: H. Okada, T. Yamamoto, and S. Shiotani, Abstracts of Papers, the Hokuriku Seminar on Synthetic Organic Chemistry in 1994, Toyama (Japan), October 1994, p. 52.
2. a) S. Shiotani, T. Kometani, K. Misuhashi, T. Nozawa, A. Kurobe, and O. Fitsukaichi, J. Med. Chem., 1976, 19, 803;
3. b) D.C. Palmer, and M.J. Strauss, Chem. Rev., 1977, 77, 1;
4. c)N. Gulavita, A. Hori, Y. Shimizu, P. Laszlo, and J. Clardy, Tetrahedron Lett., 1988, 29, 4381.
5. a) S. Takano, K. Inamoto, T. Sato, and K. Ogasawara, J. Chem. Soc., Chem. Comm., 1989, 1591;
6. b) S. Takano, K. Inamoto, T. Sato, M. Takahashi, and K. Ogasawara, J. Chem. Soc., Chem. Comm., 1990, 290.
7. T. Takemoto, M. Sodeoka, H. Sasai, and M. Shibasaki, J. Am. Chem. Soc., 1993, 115, 8477.
8. K. Nishide, Kawano, and M. Node, Proceeding of the 114th Annual Meeting of the Pharmaceutical Society of Japan, p. 65 (March 1994, in Tokyo).
9. A. N. Hulme, S. S. Henry, and A. I. Meyers, J. Org. Chem., 1995, 60, 1265.
10. Y. Génisson, C. Marazano, and B. C. Das, J. Org. Chem., 1993, 58, 2052.
11. S. Shiotani, H. Okada, T. Yamamoto, K. Nakamata, J. Adachi, and H. Nakamoto, Heterocycles, 1996, 43, 113.
12. Y. Nagao, Y. Hagiwara, T. Tohjo, Y. Hasegawa, M. Ochiai, and M. Shiro, J. Org. Chem., 1988, 53, 5986.
13. a) F.-C. Huang, L. F. H. Lee, R. S. D. Mittal, P. R. Ravikumar, J. A. Chan, C. J. Sih, E. Caspi, and C. R. Eck, J. Am. Chem. Soc., 1975, 97, 4144;
14. b) J.-L. Canet, A. Fadel, and J. Salaün, J. Org. Chem., 1992, 57, 3463;
15. c) A. Fadel, J.-L. Canet, and J. Salaün, Tetrahedron: Asymmetry, 1993, 4, 27;
16. d) L. Heiss, and H-J. Gais, Tetrahedron Lett., 1995, 36, 3833.
17. 16
18. The ee of (+)- and (-)-11 was determined by DAICEL CHIRALCEL OJ, hexane/2-propanol (97:3).
19. T. Kometani and S. Shiotani, J. Med. Chem., 1978, 21, 1105.
20. 8
21. When the double bond of 20 was hydrogenated prior to deprotection of the methoxymethyl group, the corresponding six-membered lactone was formed as a major product on treatment the hydrogenated methoxymethyl ether with acid. Treatment of the lactone with PPA did not afford the tetralone compound.
22. a) K. O. Hallinan, and T. Honda, Tetrahedtron, 1995, 51, 12211;
23. b) A. Fadel and P. Arzel, Tetrahedron: Asymmetry, 1995, 6, 893.