Enzymatic Preparation of Enantiomerically Enriched Tertiary a-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 a-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
DOIs
Publication statusPublished - 1990 Jan 1

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Enzymatic Preparation of Enantiomerically Enriched Tertiary a-Benzyloxy Acid Esters. Application to the Synthesis of (S)-(-)-Frontalin'. Together they form a unique fingerprint.

  • Cite this