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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.

SUBMITTER: Kanojia SV

PROVIDER: S-EPMC6404422 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12.

Kanojia Seema V SV Chatterjee Sucheta S Chattopadhyay Subrata S Goswami Dibakar D

Beilstein journal of organic chemistry 20190218

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][PF<sub>6</sub>], 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. ...[more]

PMID: 30873232

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