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

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Enzymatic hydrolysis
Diterpenes
Candida
Lipase
Hydrolysis
Esters
Acetates
Acids

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A synthesis of (-)-deoxypodocarpic acid methyl ester via an enzymatic enantioselective hydrolysis of the key intermidiate enol ester. / Sugai, Takeshi; Kakeya, Hideaki; Ohta, Hiromichi; Morooka, Mitsuo; Ohba, Shigeru.

In: Tetrahedron, Vol. 45, No. 19, 1989, p. 6135-6144.

Research output: Contribution to journalArticle

Sugai, Takeshi ; Kakeya, Hideaki ; Ohta, Hiromichi ; Morooka, Mitsuo ; Ohba, Shigeru. / A synthesis of (-)-deoxypodocarpic acid methyl ester via an enzymatic enantioselective hydrolysis of the key intermidiate enol ester. In: Tetrahedron. 1989 ; Vol. 45, No. 19. pp. 6135-6144.
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AU - Ohba, Shigeru

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