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.
Titolo: | Chemoenzymatic synthesis of the enantiomers of desoxymuscarine |
Autori: | CONTI, PAOLA (Primo) DALLANOCE, CLELIA MARIANGIOLA LUISA (Secondo) |
Settore Scientifico Disciplinare: | Settore CHIM/08 - Chimica Farmaceutica |
Data di pubblicazione: | 1998 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/S0957-4166(98)00010-X |
Appare nelle tipologie: | 01 - Articolo su periodico |