Application of microbial enantiofacially selective hydrolysis in natural product synthesis

Osamu Katoh, Takeshi Sugai, Hiromichi Ohta

研究成果: Article査読

26 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)1935-1944
ページ数10
ジャーナルTetrahedron: Asymmetry
5
10
DOI
出版ステータスPublished - 1994 10

ASJC Scopus subject areas

  • 触媒
  • 物理化学および理論化学
  • 有機化学
  • 無機化学

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