Enzyme-mediated synthesis of (S)- and (R)-verapamil

Authors
Brenna, E Fuganti, C Grasselli, P Serra, S
Citation
E. Brenna et al., Enzyme-mediated synthesis of (S)- and (R)-verapamil, EUR J ORG C, (7), 2001, pp. 1349-1357
Citations number
23
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
7
Year of publication
2001
Pages
1349 - 1357
Database
ISI
SICI code
1434-193X(200104):7<1349:ESO(A(>2.0.ZU;2-O
Abstract
A lipase-mediated synthesis of (S)- and (R)-verapamil is described. The key steps of the synthetic sequence are the enantioselective acetylation, medi ated by Lipase PS, of allylic alcohol (Z)-(+/-)-2, affording the acetate de rivative (Z,R)-(-)-3 (ee 92%) and the Ireland-Claisen rearrangement of this latter and of its enantiomer (Z,S)-(+)-3 (ee 92%) to afford acid derivativ es (E,R)-(-)-4 (ee 94%) and (E,S)-(+)-4 (ee 93%), pre cursors of (S)- and ( R)-verapamil, respectively.