A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12

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
• [bmim][PF6]
• DDQ
• HPA-12
• lipase