Research on Au(I)-catalyzed ene-yne cycloisomerization for construction of quassinoid scaffold

Yuta Oki, Masahisa Nakada

    Research output: Contribution to journalArticle

    1 Citation (Scopus)

    Abstract

    Compounds that undergo Au(I)-catalyzed cycloisomerizations affording tetracyclic products that can be converted into compounds with the skeleton of bruceantin are described. The Au(I)-catalyzed cycloisomerizations reported herein are hindered by a 1,3-diaxial interaction between the substituent and the methyl group in the transition state. The use of small substituents was found to increase the yield of the desired product, while the reaction of substrates with large substituents afford undesired constitutional isomers.

    Original languageEnglish
    Pages (from-to)926-929
    Number of pages4
    JournalTetrahedron Letters
    Volume59
    Issue number10
    DOIs
    Publication statusPublished - 2018 Mar 7

      Fingerprint

    Keywords

    • Au(I)-catalysis
    • Bruceantin
    • Ene-yne cycloisomerization
    • Quassinoid
    • Stereoselective

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

    Cite this