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

Article abstract of DOI:10.1246/bcsj.63.91

(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.