A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12 (Beilstein Journal of Organic Chemistry)

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. Beilstein J. Org. Chem. 2019, 15, 490–496. doi:10.3762/bjoc.15.42