Application of microbial enantiofacially selective hydrolysis in natural product synthesis

Osamu Katoh, Takeshi Sugai, Hiromichi Ohta

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Pichia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70% yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87%e.e.), to be the starting material for the synthesis of optically active natural products. Methyl (R)-3-hydroxy-12-methyltridecanoate, a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation. Final products were enantiomerically enriched to 94-95% e.e., by the lipase-mediated enantioselective transesterification, which could remove the minor enantiomer as the corresponding acetate.

Original languageEnglish
Pages (from-to)1935-1944
Number of pages10
JournalTetrahedron: Asymmetry
Volume5
Issue number10
DOIs
Publication statusPublished - 1994 Oct

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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