Enzymatic preparation of enantiomerically enriched tertiary α-benzyloxy acid esters. Application to the synthesis of (S)-(-)-frontalin

Takeshi Sugai, Hideaki Kakeya, Hiromichi Ohta

Research output: Contribution to journalArticle

63 Citations (Scopus)

Abstract

Enzymatic preparation of enantiomerically enriched tertiary α-benzyloxy acid esters is described. Enantioselective hydrolysis of the racemic esters of the formula [R-C(CH3)(OCH2Ph)CO2CH3] by lipase OF (from Candida cylindracea, Meito Sangyo Co.) was successfully carried out on a preparative scale. With the asymmetric carbon atom possessing a tertiary benzyloxy group, (S)-(-)-frontalin, a component of the aggregation pheromone of the southern pine beetle, was efficiently synthesized.

Original languageEnglish
Pages (from-to)4643-4647
Number of pages5
JournalJournal of Organic Chemistry
Volume55
Issue number15
Publication statusPublished - 1990

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Esters
Acids
Candida
Pheromones
Lipase
Hydrolysis
Carbon
Agglomeration
Atoms
frontalin

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Enzymatic preparation of enantiomerically enriched tertiary α-benzyloxy acid esters. Application to the synthesis of (S)-(-)-frontalin. / Sugai, Takeshi; Kakeya, Hideaki; Ohta, Hiromichi.

In: Journal of Organic Chemistry, Vol. 55, No. 15, 1990, p. 4643-4647.

Research output: Contribution to journalArticle

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