The first example of lipase-catalyzed resolution of a stereogenic center in steroid side chains by transesterification in organic solvent

Tetrahedron Asymmetry

Volumn 7, Issue 6, 1996, Pages 1551-1554

  Ferraboschi, Patrizia ^a   Molatore, Antonella ^a   Verza, Elisa ^a   Santaniello, Enzo ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ORGANIC SOLVENT; STEROID; TRIACYLGLYCEROL LIPASE; VINYL ACETATE;

ACYLATION; ARTICLE; ESTERIFICATION; ISOMER; PRIORITY JOURNAL;

EID: 0029884184     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00178-4     Document Type: Article

References (27)

1. (a) Faber, K.; Riva, S. Synthesis 1992, 895.
2. (b) Santaniello, E.; Ferraboschi, P.; Grisenti, P. Enzyme Microb. Technol. 1993, 15, 367.
3. (c) Fang, J.-M.; Wong, C.-H. Synlett 1994, 393.
4. (d) Carrea, G.; Ottolina, G.; Riva, S. Trends Biotechnol. 1995, 13, 63.
5. (a) Njar, V. C. O.; Caspi, E. Tetrahedron, Lett. 1987, 28, 6549.
6. (b) Riva, S.; Klibanov, A. M. J. Am. Chem. Soc. 1988, 110, 3291.
7. For recent examples, see: (a) Adamczyk, M.; Chen, Y.-Y; Fishpaugh, J. R.; Gebler, J. C. Tetrahedron: Asymmetry. 1993, 4, 1467.
8. (b) Baldessari, A.; Maier, M. S.; Gros, E. G. Tetrahedron Lett. 1995, 36, 4349. For an extensive study, see: Bertinotti, A.; Carrea, G.; Ottolina, G.; Riva, S. Tetrahedron 1994, 50, 13165.
9. (b) Baldessari, A.; Maier, M. S.; Gros, E. G. Tetrahedron Lett. 1995, 36, 4349. For an extensive study, see: Bertinotti, A.; Carrea, G.; Ottolina, G.; Riva, S. Tetrahedron 1994, 50, 13165.
10. Riva, S. in Applied Biocatalysis, Blanch, H. W.; Clark, D. S.. Eds, M. Dekker, New York 1991, Vol. 1, 179-219.
11. The lipase was a generous gift from Amano (Japan) through its italian subsidiary. We thank Mr. I. Gaudio (Mitsubishi Italia, Milano) for his kind collaboration.
12. (a) Degueil-Castaing, M.; De Jeso, B.; Drouillard, S.; Maillard, B. Tetrahedron. Lett. 1987, 28, 953.
13. (b) Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200.
14. For a recent application, see: Santaniello, E.; Ferraboschi, P.; Casati, S..; Manzocchi, Tetrahedron: Asymmetry. 1995, 6, 1521 and references cited.
15. Wicha, J.; Bal, K. J. Chem. Soc., Perkin 1 1978, 1282 and references cited herein.
16. Santaniello, E.; Ferraboschi, P.; Fiecchi, A.; Grisenti, P.; Manzocchi, A. Gazz. Chim. Ital. 1987, 117, 701.
17. R 13.9 and 14.2 min in 34:66 ratio.
18. R 14.2 min ).
19. R 14.2 min ).
20. R 14.2 min ).
21. R 14.2 min ).
22. A solution of 20 R,S-1a (0.33 g, 1 mmol) in chloroform (2.2 mL) and vinyl acetate (0.43 mL, 4.66 mmol) was added to the solid lipase (14 m g, 31.5 U/mg) under stirring at room temperarure.
23. 2O).
24. 2O).
25. Ferraboschi, P.; Casati, S.; De Grandi, S.; Grisenti, P.; Santaniello, E. Biocatalysis 1994, 10, 279.
26. A recent interpretation of the enantiopreference of Pseudomonas cepacia lipase toward primary alcohols has been proposed; see: Weissfloch, A. N. E.; Kazlauskas, R. J. J. Org. Chem. 1995, 60, 6959.
27. 2O), 5.29-5.36 (m, 1 H, CH= ).