Synthesis of an enantiomerically pure sterol side-chain precursor by enantioselective reduction of 1,3-dihydroxy-3-methyl-2-butanone with baker's yeast

✍ Scribed by Schrötter, Eberhard ;Weidner, Judith ;Schick, Hans

• Publisher: John Wiley and Sons
• Year: 1991
• Tongue: English
• Weight: 139 KB
• Volume: 1991
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199119910172

✦ Synopsis

Abstract

1,3‐Dihydroxy‐3‐methyl‐2‐butanone (1), accessible in 5 steps from 2‐methyl‐3‐butyn‐2‐ol, is reduced by baker's yeast to (R)‐(+)‐3‐methyl‐1,2,3‐butanetriol (2) with a high enantioselectivity. This chiral building block for the synthesis of various sterols with a modified side chain thus becomes available in 73% yield with an enantiomeric excess of 90%.