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
1988 Chemical and pharmaceutical bulletin  
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.
doi:10.1248/cpb.36.4337 fatcat:umviogrkyvh3fftoc6qpf3mjbu