A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12

Beilstein J Org Chem. 2019 Feb 18:15:490-496. doi: 10.3762/bjoc.15.42. eCollection 2019.

Abstract

A chemoenzymatic synthesis of the title compound has been developed using an efficient and highly enantioselective lipase-catalyzed acylation in a hydrophobic ionic liquid, [bmim][PF6], followed by a diastereoselective asymmetric dihydroxylation as the key steps for incorporating the stereogenic centers. The further conversion to the appropriate intermediates and subsequent acylation with lauric acid furnished the target compound.

Keywords: AD mix-β; DDQ; HPA-12; [bmim][PF6]; lipase.