Tetrahedron: Asymmetry

A new and efficient chemoenzymatic access to both enantiomers of 4-hydroxycyclopent-2-en-1-one

AS Demir, O Sesenoglu

Index: Demir, Ayhan S.; Sesenoglu, Ozge Tetrahedron Asymmetry, 2002 , vol. 13, # 6 p. 667 - 670

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Citation Number: 23

Abstract

A chemoenzymatic synthesis of both enantiomers of pharmacologically interesting 4- hydroxycyclopent-2-en-1-one in three steps starting from 3-methoxycyclopent-2-en-1-one is described. Manganese (III) acetate-mediated acetoxylation followed by enzyme-mediated hydrolysis of α-acetoxy enone affords acetoxy enone 3 and hydroxy enone 4 with high enantiomeric excesses and in good yields. The reduction of the acetoxy and hydroxy ...