Enzymatic synthesis of both enantiomers of 2-methylene-4- (fluoromethyl)-4-butanolides

Journal of Organic Chemistry

Volumn 63, Issue 22, 1998, Pages 8058-8061

  Komatsu, Yuzo ^a   Sasaki, Fumio ^a   Takei, Satoshi ^a   Kitazume, Tomoya ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYLENE 4 (FLUOROMETHYL) 4 BUTANOLIDE; BUTANOL; FLUORINE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHIRALITY; DRUG STABILITY; ENANTIOMER; ENZYME ACTIVITY; ENZYME SYNTHESIS; ESTERIFICATION;

EID: 0032582763     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981183z     Document Type: Article

References (17)

1. (1)(a) Filler, R.; Kobayashi, Y. Biomedicinal Aspects of Fluorine Chemistry; Kodansha Elsevier Biomedical: Tokyo, 1982.
2. (b) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley & Sons: New York, 1991.
3. Kollonitsch, J. Isr. J. Chem. 1978, 17, 53.
4. Bey, P.; Gerhart, F.; von Dorsselaer, V.; Danzin, C. J. Med. Chem. 1983, 26, 1551.
5. Casara, P. J.; Kenny, M. T.; Jund, K. C. Tetrahedron Lett. 1991, 32, 3823.
6. Yamazaki, T.; Haga, J.; Kitazume, T. Bioorg. Med. Chem. Lett. 1991, 1, 271.
7. Itoh, K.; Takeda, M.; Namekawa, M.; Nayuki, S.; Murayama, Y.; Yamazaki, T.; Kitazume, T. Chem. Lett., 1995, 641 and references therein.
8. Welch, J. T. Tetrahedron 1987, 43, 3123.
9. Fearon, K.; Spaltenstein, A.; Hopkins, P. B.; Gelb, M. H. J. Med. Chem. 1987, 30, 1617.
10. Abeles, R. H.; Maycock, A. L. Ace. Chem. Res. 1976, 9, 313.
11. Ohta, H.; Tetsukawa, H.; Noto, N. J. Org. Chem. 1982, 47, 2400.
12. Gutman, A. L.; Bravdo, T. J. Org. Chem. 1989, 54, 4263.
13. Fukusaki, E.; Senda, S.; Nakazono, Y.; Omata, T. Tetrahedron 1991, 47, 6223.
14. Kitazume T.; Yamazaki, T. Topics in Current Chemistry; Springer: Berlin, Germany, 1997; Vol. 193, p 91 and references therein.
15. Lin, J.-T.; Yamazaki, T.; Kitazume, T. J. Org. Chem. 1987, 52, 3211.
16. Murata, K.; Kaneko, S.; Kitazume, T. Bioorg. Med. Chem. Lett. 1993, 3, 2685.
17. Murata, K.; Kitazume, T. Tetrahedron: Asymmetry 1993, 4. 889.