Novel Synthesis of Optically Pure Anthracyclinone Intermediates by the Use of Microbial Asymmetric Reduction with Fermenting Baker's Yeast

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概要

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• Microbial reduction of the racemic α-hydroxy ketones ((±)-3a, b) with fermenting baker's yeast was found to afford diastereomeric mixtures of the vicinal-diols ((-)-4a, b) and ((+)-5a, b) in 90 and 91% yields, respectively. Separation of these diastereomers was readily accomplished by fractional recrystallization, giving pure (-)-4a, b and mixtures of (-)-4a, b and (+)-5a, b. Oxidation of these samples furnished optically pure anthracyclinone intermediates ((R)-(-)-3a, b) and their partially optically active antipodes ((S)-(+)-3a, b). The undesired enantiomers ((S)-(+)-3a, b) and vicinal-diols ((+)-5a, b) could be recycled to (±)-3a, b and the prochiral ketones (6a, c) by racemization with p-toluenesulfonic acid and oxidative cleavage with sodium metaperiodate, respectively. Another important optically pure anthracyclinone intermediate ((R)-(-)-3c) was prepared from (R)-(-)-3a, b according to the reported method.

• 公益社団法人日本薬学会の論文
• 1984-11-25

著者

• 寺島 孜郎

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 寺島 孜郎

  (財)相模中央化学研究所

• 寺島 孜郎

  Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Address)sagami Chemical Research Cen

• 田本 克己

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 田本 克巳

  Development Research Laboratories I Sumitomo Pharmaceuticals Research Center

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