A synthesis of (-)-sitophilate by utilizing yeast-mediated reduction of an enol ester

Takeshi Sugai, Daisuke Sakuma, Naoki Kobayashi, Hiromichi Ohta

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

The microbial reduction of 1′-ethylpropyl 2-methyl-3-oxopentanoate, a β-keto ester possessing bulky substituent, as well as the corresponding enol ester was examined. Epimeric mixture of hydroxy ester, containing (2S,3S-isomer as the major product (92%e.e., 43%d.e.) was obtained via the reduction of enol ester with growing cells of Pichia farinosa IAM 4682 in 63% yield. The resulting β-hydroxy ester was converted to (2S,3R)-isomer (88%e.e., 96%d.e.), of which e.e. was further enhanced by the lipase-catalyzed partial hydrolysis of the corresponding chloroacetate to give (-)-sitophilate, (99%e.e., 98%d.e.) an aggregation pheromone of Sitophillus granarius L.

Original languageEnglish
Pages (from-to)7237-7244
Number of pages8
JournalTetrahedron
Volume47
Issue number35
DOIs
Publication statusPublished - 1991 Aug 26

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Yeast
Esters
Yeasts
Isomers
Pichia
Pheromones
Lipase
Hydrolysis
Agglomeration
sitophilate

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A synthesis of (-)-sitophilate by utilizing yeast-mediated reduction of an enol ester. / Sugai, Takeshi; Sakuma, Daisuke; Kobayashi, Naoki; Ohta, Hiromichi.

In: Tetrahedron, Vol. 47, No. 35, 26.08.1991, p. 7237-7244.

Research output: Contribution to journalArticle

Sugai, Takeshi ; Sakuma, Daisuke ; Kobayashi, Naoki ; Ohta, Hiromichi. / A synthesis of (-)-sitophilate by utilizing yeast-mediated reduction of an enol ester. In: Tetrahedron. 1991 ; Vol. 47, No. 35. pp. 7237-7244.
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