Stereoselective synthesis of malyngic acid and fulgidic acid

Yusuke Kurashina, Ayako Miura, Masaru Enomoto, Shigefumi Kuwahara

    Research output: Contribution to journalArticlepeer-review

    18 Citations (Scopus)

    Abstract

    A new stereoselective total synthesis of malyngic acid has been achieved from a known oxazolidinone derivative via eight steps involving the Evans asymmetric alkylation as the chirality-inducing step and chelation-controlled Zn(BH4)2 reduction of an α-hydroxy ketone intermediate for the installation of the 12,13-anti stereochemistry. Fulgidic acid, the C12-epimer of malyngic acid, has also been synthesized in eight steps from the same starting material by using syn-selective K-Selectride reduction of an α-alkoxy ketone intermediate.

    Original languageEnglish
    Pages (from-to)1649-1653
    Number of pages5
    JournalTetrahedron
    Volume67
    Issue number9
    DOIs
    Publication statusPublished - 2011 Mar 4

    Keywords

    • Diastereoselective reduction
    • Fulgidic acid
    • Malyngic acid
    • Oxylipin
    • Total synthesis

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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