Enantioselective synthesis of (-)- and (+)-conduritol F via enzymatic asymmetrization of cis-cyclohexa-3,5-diene-1,2-diol

Journal of Organic Chemistry

Volumn 61, Issue 18, 1996, Pages 6458-6461

  Patti, Angela ^a   Sanfilippo, Claudia ^a   Piattelli, Mario ^a   Nicolosi, Giovanni ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA GLUCOSIDASE INHIBITOR; CONDURITOL F; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVITY; REACTION ANALYSIS;

EID: 0029831967     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960251j     Document Type: Article

References (27)

1. For a review, see: Balci, M.; Sütbeyaz, Y.; Seçen, H. Tetrahedron 1990, 46, 3715.
2. (a) Ley, S. V.; Sternfeld, F.; Taylor, S. Tetrahedron Lett. 1987, 28, 225.
3. (b) Hudlicky, T.; Price, J. D.; Rulin, F.; Tsunoda, T. J. Am. Chem. Soc. 1990, 112, 9439.
4. Ley, S. V.; Sternfeld, F. Tetrahedron Lett. 1988, 29, 5305.
5. Ley, S. V.; Yeung, L. L. Synlett. 1992, 997.
6. Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319.
7. Ley, S. V.; Redgrave, A. J. Synlett. 1990, 393.
8. (a) Hudlicky, T.; Price, J. D.; Olivo, H. F. Synlett. 1991, 645.
9. (b) Carless, H. A. J.; Oak, O. Z. J. Chem. Soc., Chem. Commun. 1991, 61.
10. (c) Hudlicky, T.; Luna, H.; Olivo, H. F.; Andersen, C.; Nugent, T.; Price, J. D. J. Chem. Soc. Perkin Trans. 1 1991, 2907.
11. (d) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795.
12. (e) Carless, H. A. J. Tetrahedron Lett. 1992, 33, 6379.
13. (f) Carless, H. A. J. J. Chem. Soc., Chem. Commun. 1992, 234.
14. (a) Johnson, C. R.; Plè, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006.
15. (b) Dumortier, L.; Liu, P.; Dobbelaere, S.; Van der Eycken, J.; Vandewalle, M. Synlett. 1992, 243.
16. (c) Pingli L., Vandewalle, M., Tetrahedron 1994, 50, 7061.
17. Patti, A.; Nicolosi, G.; Piattelli M.; Sanfilippo, C. Tetrahedron: Asymmetry 1995, 6, 2195.
18. Nicolosi, G.; Patti, A.; Piattelli M.; Sanfilippo, C. Tetrahedron Lett. 1995, 36, 6545.
19. Nicolosi, G.; Patti, A.; Piattelli M.; Sanfilippo, C. Tetrahedron: Asymmetry 1995, 6, 519.
20. Wang, Y.-F.; Chen, C.-H.; Girdaukas, G.; Sih, C. J. J.. Am. Chem. Soc. 1984, 106, 3695.
21. Carless, H. A. J.; Busia K.; Dove Y.; Malik S. S. J. Chem. Soc. Perkin Trans. 1 1993, 2505.
22. (a) Cha , J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3943.
23. (b) Cha , J. K.; Christ, W. J.; Kishi, Y. Tetrahedron 1984, 40, 2247.
24. Milas, N. A.; Sussman, S. J. Am. Chem. Soc. 1936, 58, 1302.
25. (a) Schröder, M. Chem. Rev. 1980, 80, 187.
26. (b) VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 23, 1973.
27. Le Drian, C.; Vieira, E; Vogel, P. Helv. Chim. Acta 1989, 72, 338.