A synthesis of (-)-deoxypodocarpic acid methyl ester via an enzymatic enantioselective hydrolysis of the key intermidiate enol ester

Takeshi Sugai, Hideaki Kakeya, Hiromichi Ohta, Mitsuo Morooka, Shigeru Ohba

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

(1R, 4aR, 10aS)-(-)-1-Methoxycarbonyl-1, 4a-dimethyl-1,2,3,4,4a,9,10, 10a-octahydrophenanthrene (deoxypodocarpic acid methyl ester 1), a useful intermediate for the synthesis of various diterpenes, was synthesized from (R)-(+)-6-ethoxycarbonyl-2, 6-dimethyl-1-cyclohexenyl acetate 4. The chiral starting material was prepared by the enantioselective hydrolysis of the corresponding racemate using lipase OF from Candida cylindracea.

Original languageEnglish
Pages (from-to)6135-6144
Number of pages10
JournalTetrahedron
Volume45
Issue number19
DOIs
Publication statusPublished - 1989

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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