Bulletin of the Chemical Society of Japan p. 91 - 96 (1990)
Update date:2022-08-03
Topics: Isolation and Purification Synthesis of Natural Products Cultivation of Microorganisms Isolation of Enzymes Bioreduction of (S)-4-nitro-2-butanol
Nakamura
Kitayama
Inoue
Ohno
(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 condensations with Michael acceptors or aldehydes is largely affected by a base employed as the catalyst.
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Doi:10.1016/0008-6215(90)80053-6
(1990)Doi:10.1021/bi101808h
(2011)Doi:10.1248/cpb.38.1479
(1990)Doi:10.1002/jhet.391
(2011)Doi:10.1055/s-1990-27010
(1990)Doi:10.1016/j.tetlet.2011.02.104
(2011)