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.
Chemoenzymatic synthesis of the enantiomers of desoxymuscarine / P. Conti, C. Dallanoce, M. De Amici, C. De Micheli, G. Carrea, F. Zambianchi. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 9:4(1998), pp. 657-665. [10.1016/S0957-4166(98)00010-X]
Chemoenzymatic synthesis of the enantiomers of desoxymuscarine
P. ContiPrimo
;C. DallanoceSecondo
;M. De Amici;C. De Micheli;
1998
Abstract
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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