Biocatalytic reduction of a racemic selenocyclohexanone by Brazilian basidiomycetes

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• 作者：Le ; ro Piovan ; Marina Capelari ; Le ; ro H. Andrade ; Joã ; o V. Comasseto ; André ; L.M. Porto
• 关键词：Cyclizations ; Heterocycles ; Medium-sized rings ; Ring-closing metathesis ; Silyl enol ethers
• 刊名：Tetrahedron ; Asymmetry
• 出版年：2007
• 期刊代码：108_09574166
• 类别：ch
• 出版时间：4 July 2007
• 卷：18
• 期：12
• 页码：1398-1402
• 文件大小：210 K

摘要

An efficient synthesis of the chiral cyclic secondary alcohols, trans-2-(phenylseleno)cyclohexanol 1a and cis-2-(phenylseleno)cyclohexanol 1a, was obtained by enzymatic reduction of 2-(phenylseleno)cyclohexanone 1 using whole fungal cells. Five strains of white-rot basidiomycetes were examined; Irpex lacteus CCB 196, Pycnoporus sanguineus CCB 196, Trametes rigida CCB 285, Trametes versicolor CCB 202 and Trichaptum byssogenum CCB 203. Cells of T. rigida CCB 285 gave alcohols cis-(RS)-1a and trans-(SS)-1a in high enantiomeric excesses (ca. 99%).