Enzyme??Mediated Synthesis of (S)??and (R)??Verapamil

E Brenna, C Fuganti, P Grasselli…

Index: Brenna, Elisabetta; Fuganti, Claudio; Grasselli, Piero; Serra, Stefano European Journal of Organic Chemistry, 2001 , # 7 p. 1349 - 1357

Full Text: HTML

Citation Number: 15

Abstract

Abstract A lipase-mediated synthesis of (S)-and (R)-verapamil is described. The key steps of the synthetic sequence are the enantioselective acetylation, mediated by Lipase PS, of allylic alcohol (Z)-(±)-2, affording the acetate derivative (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 derivatives (E, R)-(−)-4 (ee 94%) and (E, S)-(+)-4 (ee 93%), precursors of (S)- ...