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

HIROSHI SUEMUNE; TETSUJI HARABE; ZHUO-FENG XIE; KIYOSHI SAKAI

doi:10.1248/cpb.36.4337

HIROSHI SUEMUNE, TETSUJI HARABE, ZHUO-FENG XIE, KIYOSHI SAKAI

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Keywords: asymmetric synthesis, enzymatic hydrolysis, meso compound, electric eel cholinesterase, (-)-malyngolide

JOURNAL FREE ACCESS

1988 Volume 36 Issue 11 Pages 4337-4344

DOI https://doi.org/10.1248/cpb.36.4337

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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.

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