Stereoselective construction of the ABC-ring system of fusidane triterpenes via intermolecular/transannular Michael reaction cascade

Tomohiro Fujii, Masahisa Nakada

    Research output: Contribution to journalArticle

    4 Citations (Scopus)

    Abstract

    A stereoselective construction of the ABC-ring system of fusidane triterpenes via intermolecular/transannular Michael reaction cascade is described. The substrate, a ten-membered carbocyclic ketone, has been successfully prepared by the Cr-mediated intramolecular alkenylation of the corresponding acyclic compound. The array of functionalities in the product stereoselectively obtained by the cascade reaction is useful for further structural modifications directed toward the total synthesis of fusidane and other triterpenes, and designed molecules intended for studying structure-activity relationships.

    Original languageEnglish
    Pages (from-to)1597-1601
    Number of pages5
    JournalTetrahedron Letters
    Volume55
    Issue number9
    DOIs
    Publication statusPublished - 2014 Feb 26

    Fingerprint

    Triterpenes
    Alkenylation
    Structure-Activity Relationship
    Ketones
    Molecules
    Substrates

    Keywords

    • Fusidane
    • Intermolecular
    • Michael reaction
    • Stereoselective
    • Transannular

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Stereoselective construction of the ABC-ring system of fusidane triterpenes via intermolecular/transannular Michael reaction cascade. / Fujii, Tomohiro; Nakada, Masahisa.

    In: Tetrahedron Letters, Vol. 55, No. 9, 26.02.2014, p. 1597-1601.

    Research output: Contribution to journalArticle

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