Asymmetric synthesis of both enantiomers of fluoxetine via microbiological reduction of ethyl benzoylacetate

Abstract

Microbiological reduction of ethyl benzoylacetate by bakers' yeast (Saccharomyces cerevisiae), Beauveria sulfurescens or Geotrichum candidum afforded ethyl (S)-3-hydroxy-3-phenylpropionate in high optical yield. This enantiomerically pure alcohol was converted into both enantiomers of fluoxetine (7). The product resulting from the bakers' yeast reduction had ee values (87-93%) lower than the 100% value erroneously attributed in earlier studies. © 1992.