Three-component synthesis of polysubstituted benzene derivatives via Diels-Alder reaction of cyclopentadienone acetal with alkyne

Sota Sato, Hiroyuki Isobe, Takatsugu Tanaka, Tomohiko Ushijima, Eiichi Nakamura

    Research output: Contribution to journalArticle

    28 Citations (Scopus)

    Abstract

    An efficient and regioselective synthesis of polysubstituted benzene derivatives was achieved via multicomponent reaction of a substituted cyclopropenone acetal and two alkyne molecules. The synthesis utilizes cyclopentadienone acetal as an intermediate and enables regioselective [2+2+2] assembly of the three-components into a benzene ring. A variety of polysubstituted benzene derivatives of synthetic and structural interest have been synthesized.

    Original languageEnglish
    Pages (from-to)11449-11455
    Number of pages7
    JournalTetrahedron
    Volume61
    Issue number48
    DOIs
    Publication statusPublished - 2005 Nov 28

    Keywords

    • Cyclopentadiene
    • Cyclopropene
    • Diels-Alder reaction
    • Polysubstituted benzene
    • Three-component [2+2+2] synthesis

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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