Yeast-mediated synthesis of optically active diols with C2-symmetry and (R)-4-pentanolide

Hajime Ikeda, Eriko Sato, Takeshi Sugai, Hiromichi Ohta

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Abstract

Reduction of some diketones and a ketoacid with yeast, Pichia farinosa IAM 4682 was examined. The reduction of carbonyl groups proceeded highly selectively with an anti-Prelog fashion to give (R)-alcohols. (2R,5R)-2,5-Hexanediol (83% yd., >99% e.e., 95% d.e.), (2R,4R)-2,4-pentanediol (94% yd., >99% e.e., 98% d.e.), and (R)-pentanolide (67% yd., >99% e.e.) were highly efficiently obtained from the corresponding ketones. Effect of the structure of substrate on the stereochemical course as well as the selectivity were discussed.

Original languageEnglish
Pages (from-to)8113-8122
Number of pages10
JournalTetrahedron
Volume52
Issue number24
DOIs
Publication statusPublished - 1996 Jun 10

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ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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