Research on Liebeskind-Srogl coupling/intramolecular Diels-Alder reaction cascade

Tomohiro Fujii, Yuta Oki, Masahisa Nakada

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    Abstract

    The Liebeskind-Srogl coupling/intramolecular Diels-Alder (IMDA) reaction cascade that stereoselectively affords a tricarbocyclic compound with a trans–trans-cis fused ring system including an all-carbon quaternary stereogenic center at the ring junction is described. The cascade reactions proceed quickly and stereoselectively afford the products within 2 h at room temperature in the presence of a suitable thioester. The developed protocol as well as the prepared chiral compounds are useful for the enantioselective total synthesis of terpenoids with the trans–trans-cis fused ring system.

    Original languageEnglish
    Pages (from-to)882-886
    Number of pages5
    JournalTetrahedron Letters
    Volume59
    Issue number10
    DOIs
    Publication statusPublished - 2018 Mar 7

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    Keywords

    • Cascade
    • Diels-Alder
    • Intramolecular
    • Liebeskind-Srogl
    • Stereoselective

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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