Stereochemical control in microbial reduction. 12.(S)-4-nitro-2-butanol as a source to synthesize natural products.

K Nakamura, T Kitayama, Y Inoue, A Ohno

Index: Nakamura; Kitayama; Inoue; Ohno Bulletin of the Chemical Society of Japan, 1990 , vol. 63, # 1 p. 91 - 96

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Citation Number: 24

Abstract

(S)-(+)-4-Nitro-2-butanol (1) obtained by the stereoselective reduction of 4-nitro-2-butanone by bakers' yeast was employed for the syntheses of natural products. A precursor of (+)- brefeldin A is synthesized starting from this chiral building block by 10 steps short-cut procedure compared with the shortest method so far reported.(S)-(+)-Sulcatol is obtained in much better enantiomeric purity than those reported. The reactivity of 1 in base-catalyzed ...