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 journalArticlepeer-review

    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 - 2001 Sep

    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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