Total Synthesis of (+)‐Scyphostatin, a Potent and Specific Inhibitor of Neutral Sphingomyelinase

Abstract

The five crucial steps in the first total synthesis of (+)-scyphostatin from D-arabinose involve (see picture): a) stereoselective aldol coupling to form a quaternary stereocenter, b) ring-closing metathesis (RCM) to construct the cyclohexene ring, c) Negishi coupling for the preparation of the fatty acid side chain, d) amide formation to connect the cyclohexene and fatty acid segments, e) stereospecific epoxide-ring formation.