Syntheses of Highly Oxygen-functionalized Derivatives of Dihydrodihydroxyphthalic Acid in Enantiomerically Enriched Forms

Hajime Ikeda, Hiroyuki Hosomi, Shigeru Ohba, Hiromichi Ohta, Takeshi Sugai

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Starting from dihydrodihydroxyphthalic acid (DDP), (1R, 2S, 5R, 6S))-(-)-3,4-bis(benzyloxymethyl)-5-hydroxy-8,8-dimethyl-6,8-dioxabicyelo[4.3.0]non-3-en-2-yl chloroacetate (>95%e.e.), a highly oxygen-functionalized derivative, was prepared by a combination of chemical and enzymatic reactions. The key step for asymmetrization was hydrolysis of the corresponding meso bis-chloroacetate with pig pancreatic lipase.

Original languageEnglish
Pages (from-to)396-400
Number of pages5
JournalBioscience, Biotechnology and Biochemistry
Volume62
Issue number2
DOIs
Publication statusPublished - 1998 Jan 1

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Keywords

  • dihydrodihydroxyphthalic acid
  • hydrolysis
  • meso substrate
  • photooxygenation
  • pig pancreatic lipase

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

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