Enzymatic Hydrolysis of 2,2-Bis(acetoxymethyl)cycloalkanones, and Its Application to Formal Synthesis of (—)-Malyngolide

Abstract

Asymmetric hydrolysis of 2,2-bis(acetoxymethyl)cyclopentanone (5) using biocatalysts and its application to a formal synthesis of (-)-malyngolide are described. For the asymmetric induction at the quaternary carbon of 5, cholinesterase from electric eel was found to be effective to afford the (+)-monoacetate (6) (90%ee). Compound (+)-6 was easily converted to the synthetic intermediate (28) for (—)-malyngolide. © 1988, The Pharmaceutical Society of Japan. All rights reserved.