Chemoenzymatic synthesis of the enantiomers of desoxymuscarine

Two different chemoenzymatic approaches allowed the preparation of the enantiomers of desoxymuscarine 5, a muscarinic receptor agonist. Transesterification of racemic 5-hexen-2-ol 7 with vinyl butyrate under the catalysis of Candida antarctica B lipase was the key step for the preparation of (-)-5 (...

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Bibliographic Details
Published in:Tetrahedron: Asymmetry
Main Authors: P. Conti, C. Dallanoce, M. De Amici, C. De Micheli, G. Carrea, F. Zambianchi
Format: Article in Journal/Newspaper
Language:English
Published: PERGAMON-ELSEVIER SCIENCE LTD 1998
Subjects:
Settore CHIM/08 - Chimica Farmaceutica
Antarc*
Antarctica
Online Access:http://hdl.handle.net/2434/183323
https://doi.org/10.1016/S0957-4166(98)00010-X
Description
Summary:Two different chemoenzymatic approaches allowed the preparation of the enantiomers of desoxymuscarine 5, a muscarinic receptor agonist. Transesterification of racemic 5-hexen-2-ol 7 with vinyl butyrate under the catalysis of Candida antarctica B lipase was the key step for the preparation of (-)-5 (2R,5R). On the other hand, lipase PS-catalyzed hydrolysis of iodo butyrate (+/-)-14 was utilized to obtain (+)-5 (2S,5S). Both enantiomers were prepared with enantiomeric excesses higher than 98\%. (C) 1998 Elsevier Science Ltd. All rights reserved.

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