Synthesis of lupinacidins A and B via sequential cycloaddition-double elimination

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    3 Citations (Scopus)

    Abstract

    The first synthesis of lupinacidins A and B, tumor cell invasion inhibitors of microbial origin, has been achieved in four operational steps from 3-methoxy-2-methyl-2-cyclohexenone via the Diels-Alder cycloaddition of a conjugated cyclohexadiene derivative with a juglone-derived sulfinyl quinone followed by sequential elimination of a sulfenic acid and ethylene to afford protected forms of the target molecules.

    Original languageEnglish
    Pages (from-to)4570-4572
    Number of pages3
    JournalTetrahedron Letters
    Volume51
    Issue number34
    DOIs
    Publication statusPublished - 2010 Aug 25

    Keywords

    • Anthraquinone
    • Antitumor
    • Diels-Alder reaction
    • Lupinacidin

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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