Reduction of bicyclo[3.3.1]nonane-2,8-diones with baker's yeast.
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.
Mori
K
K
Department of Agricultural Chemistry, University of Tokyo, Japan.
Takayama
S
S
Kido
M
M
D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003512:Cyclohexanones / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011048:Polarography; D012441:Saccharomyces cerevisiae / Q000378:metabolism*; D013329:Structure-Activity Relationship
D001643:Bridged Bicyclo Compounds; D003512:Cyclohexanones; D007202:Indicators and Reagents