Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
The Use of Microorganisms in Organic Synthesis. I. Microbiological Asymmetric Reduction of 2-Methyl-3-oxobutyrates
秋田 弘幸古市 昭也越地 弘子堀越 弘毅大石 武
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キーワード: yeast
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1983 年 31 巻 12 号 p. 4376-4383

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The synthesis of optically active α-methyl β-hydroxy esters I by means of microbiological reduction of the corresponding β-keto esters II was carried out. Benzyl 2-methyl-3-oxobutyrate 1 was found to be reduced by a variety of yeasts to the α-methyl β-hydroxy esters with (2R, 3S)- and (2S, 3S)-configurations (2 and 3, respectively), and by carrying out screening experiments, yeasts which give each product with high optical purity were isolated. Moreover, the absolute configuration and the optical purity of the reduction products were found to be determinable from the 400 MHz nuclear magnetic resonance spectra of the (+)-α-methyoxy-α-trifluoromethylphenylacetyl esters of the alcohols produced.

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© The Pharmaceutical Society of Japan
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