Cross-metathesis approach to a (2E,4E)-dienoic acid intermediate for the synthesis of elaiolide

Akira Morita, Shigefumi Kuwahara

    Research output: Contribution to journalArticlepeer-review

    20 Citations (Scopus)

    Abstract

    A (2E,4E)-7-hydroxy-2,4-dienoic acid, previously employed as a key intermediate for the total synthesis of the macrodiolide antibiotic elaiolide, was prepared stereoselectively and concisely from (S)-2-methyl-3-trityloxypropanal by a three-step sequence consisting of Brown's asymmetric crotylboration, olefin cross-metathesis, and alkaline treatment. Ethyl 3-pivaloyloxy-4-pentenoate was used as a masked dienoate in the cross-metathesis step.

    Original languageEnglish
    Pages (from-to)3163-3166
    Number of pages4
    JournalTetrahedron Letters
    Volume48
    Issue number18
    DOIs
    Publication statusPublished - 2007 Apr 30

    Keywords

    • 2,4-Alkadienoic acid
    • Antibiotic
    • Cross-metathesis
    • Elaiolide
    • Enantioselective synthesis

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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