A concise synthesis of pinellic acid using a cross-metathesis approach

Ayako Miura, Shigefumi Kuwahara

    Research output: Contribution to journalArticlepeer-review

    30 Citations (Scopus)

    Abstract

    A new enantioselective synthesis of pinellic acid, a trihydroxy unsaturated fatty acid exhibiting oral adjuvant activity for nasally administered influenza vaccine, has been accomplished using a cross-metathesis reaction between two terminal olefin intermediates as the key step. This synthesis is the shortest to date, furnishing pinellic acid in 17% overall yield via only seven steps from a readily available known dihydroxy ester.

    Original languageEnglish
    Pages (from-to)3364-3368
    Number of pages5
    JournalTetrahedron
    Volume65
    Issue number17
    DOIs
    Publication statusPublished - 2009 Apr 25

    Keywords

    • Cross-metathesis
    • Fatty acid
    • Influenza
    • Pinellic acid
    • Total synthesis

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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