Application of a 6π-1-azatriene electrocyclization strategy to the total synthesis of the marine sponge metabolite ageladine A and biological evaluation of synthetic analogues

Matthew L. Meketa, Steven M. Weinreb, Youichi Nakao, Nobuhiro Fusetani

    Research output: Contribution to journalArticle

    32 Citations (Scopus)

    Abstract

    (Chemical Equation Presented) A 12-step synthesis of the angiogenesis inhibitory marine metabolite ageladine A is reported. The key steps include a 6π-1-azatriene electrocyclization for formation of the pyridine ring and a Suzuki-Miyaura coupling of N-Boc-pyrrole-2-boronic acid with a chloroimidazopyridine. In addition, an assessment of the biological activity of a variety of synthetic analogues of ageladine A prepared during this synthesis is described.

    Original languageEnglish
    Pages (from-to)4892-4899
    Number of pages8
    JournalJournal of Organic Chemistry
    Volume72
    Issue number13
    DOIs
    Publication statusPublished - 2007 Jun 22

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    Metabolites
    Boronic Acids
    Pyrroles
    Bioactivity
    Ageladine A
    pyridine

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

    Application of a 6π-1-azatriene electrocyclization strategy to the total synthesis of the marine sponge metabolite ageladine A and biological evaluation of synthetic analogues. / Meketa, Matthew L.; Weinreb, Steven M.; Nakao, Youichi; Fusetani, Nobuhiro.

    In: Journal of Organic Chemistry, Vol. 72, No. 13, 22.06.2007, p. 4892-4899.

    Research output: Contribution to journalArticle

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    AU - Fusetani, Nobuhiro

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