Synthesis of (-)-Methyl Shikimate via Enzymatic Resolution of (1S*, 4R*, 5R*)-4-Hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one

Takayuki Oritani, Rumi Ueda, Hiromasa Kiyota

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The synthesis of methyl (-)-shikimate [(-)-2] was achieved via lipase-catalyzed optical resolution of (1S*, 4R*, 5R*)-4-hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one (3). Transesterification of (±)-3 and vinyl acetate with lipase MY and subsequent hydrolysis gave optically pure (-)-3. This compound was converted to (-)-2 in two steps.

Original languageEnglish
Pages (from-to)2106-2109
Number of pages4
JournalBioscience, Biotechnology and Biochemistry
Volume65
Issue number9
DOIs
Publication statusPublished - Sep 1 2001
Externally publishedYes

Keywords

  • (1S*, 4R*, 5R*)-4-hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one
  • Hydrolysis
  • Lipase
  • Shikimic acid
  • Transesterification

ASJC Scopus subject areas

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

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