A highly stereoselective intramolecular Diels-Alder reaction for construction of the AB ring moiety of bruceantin

Kenji Usui, Takahiro Suzuki, Masahisa Nakada

    Research output: Contribution to journalArticle

    6 Citations (Scopus)

    Abstract

    A highly stereoselective intramolecular Diels-Alder (IMDA) reaction for the construction of the AB ring moiety of bruceantin is described. The product of the IMDA reaction comprises a trans-AB ring junction and stereotetrad including an all carbon quaternary stereogenic center, wherein three stereogenic centers correspond to those of bruceantin. Functional groups embedded in the product are suitable for a variety of transformations. Hence, this IMDA product could be a useful intermediate for the enantioselective total synthesis of not only bruceantin, but also other bioactive compounds.

    Original languageEnglish
    Pages (from-to)1247-1251
    Number of pages5
    JournalTetrahedron Letters
    Volume56
    Issue number10
    DOIs
    Publication statusPublished - 2015 Mar 4

    Fingerprint

    Cycloaddition Reaction
    Alnus
    Functional groups
    Carbon
    bruceantin

    Keywords

    • Diels-Alder reaction
    • Intramolecular
    • Natural product
    • Stereoselective
    • Synthesis

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    A highly stereoselective intramolecular Diels-Alder reaction for construction of the AB ring moiety of bruceantin. / Usui, Kenji; Suzuki, Takahiro; Nakada, Masahisa.

    In: Tetrahedron Letters, Vol. 56, No. 10, 04.03.2015, p. 1247-1251.

    Research output: Contribution to journalArticle

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