Biocatalytic reduction of a racemic selenocyclohexanone by Brazilian basidiomycetes

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%).

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trans-(1S,2S)-2-(Phenylseleno)cyclohexanolC12H16SeOEe = 99%[α]D25=+44.8 (c 0.53, CHCl3)Absolute configuration: (S,S)

cis-(1S,2S)-2-(Phenylseleno)cyclohexanolC12H16SeOEe = 99%[α]D25=+10.1 (c 0.42, CHCl3)Absolute configuration: (R,S)