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.
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
Kyushu University
Chemical and Pharmaceutical Bulletin
1988 年
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