A Chemoenzymatic Approach to the Stereocontrolled Synthesis of the C1–C11 fragment of (+)‐Peloruside A

Abstract

AbstractA highly efficient and diastereoselective synthesis of the C1–C11 fragment of the marine natural product (+)‐peloruside A has been developed. Through enzymatic desymmetrization of diethyl 3‐hydroxyglutarate with lipase B from Candida antarctica a large‐scale access to enantiomerically highlyenriched starting material was achieved. Subsequent stereogenerating key steps utilized in the synthesis were a Sharpless asymmetric dihydroxylation and a doubly diastereoselective Mukaiyama aldol reaction to set up thestereogenic centers at C2, C3, C5, C7 and C8 with correct absolute configuration.