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Reduction of bicyclo[3.3.1]nonane-2,8-diones with baker's yeast
1Department of Agricultural Chemistry, University of Tokyo, Japan.
Bioorganic & Medicinal Chemistry
|June 1, 1994
Abstract:
Reduction of bicyclo[3.3.1]nonane-2,8-dione (1) and its homologues 2 and 3 with baker's yeast affords (1R,5S,8S)-8-hydroxybicyclo[3.3.1]nonan-2-one (4) and its higher homologues 5 and 6 with ca 97% e.e. in 72-86% yields. The absolute configuration of 5 was confirmed by the X-ray crystallographic analysis of its camphanic ester 22.