A CHEMOENZYMATIC SYNTHESIS OF BOTH ENANTIOMERS OF A CIS-LIGNAN LACTONE

Authors
CHENEVERT R ROSE YS
Citation
R. Chenevert et Ys. Rose, A CHEMOENZYMATIC SYNTHESIS OF BOTH ENANTIOMERS OF A CIS-LIGNAN LACTONE, Tetrahedron : asymmetry, 9(16), 1998, pp. 2827-2831
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
16
Year of publication
1998
Pages
2827 - 2831
Database
ISI
SICI code
0957-4166(1998)9:16<2827:ACSOBE>2.0.ZU;2-Z
Abstract
The stereoselective acetylation of meso-2,3-bis(3,4-dimethoxybenzyl)bu tanediol by vinyl acetate in the presence of Candida antarctica lipase in benzene gave the corresponding (+)-(2S,3R) monoester (ee greater t han or equal to 98%). Transesterification of meso-2,3-bis(3,4-dimethox ybenzyl)butyl diacetate, in the presence of the same enzyme, by ethano l in benzene/isopropyl ether gave the corresponding (-)-(2R,3S) monoes ter (ee greater than or equal to 98%). Both enantiomers of the known c is-2,3-bis(3,4-dimethoxybenzyl)butyrolactone were synthesized from the se monoesters. (C) 1998 Elsevier Science Ltd. AII rights reserved.