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  • Syntheses of Showdomycin and its Anomer Using N-(Triisopropylsilyl)pyrrole as a Synthetic Equivalent for the Maleimide C3-Anion

    Author(s)
    L. Hungerford, Natasha
    J. Armitt, David
    G. Banwell, Martin
    Griffith University Author(s)
    Hungerford, Natasha L.
    Year published
    2004
    Metadata
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    Abstract
    Showdomycin (1) and its anomer (2) have been prepared in four steps from readily available trichloroacetimidate 9.The key step involves reaction of the last compound with the title pyrrole 3 so as to form a chromatographically separable mixture of the pyrrole C-glycosides 10 and 11. Thesepyrroles are desilylated then oxidized to the corresponding maleimides using PCC.Showdomycin (1) and its anomer (2) have been prepared in four steps from readily available trichloroacetimidate 9.The key step involves reaction of the last compound with the title pyrrole 3 so as to form a chromatographically separable mixture of the pyrrole C-glycosides 10 and 11. Thesepyrroles are desilylated then oxidized to the corresponding maleimides using PCC.
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    Journal Title
    Synthesis: journal of synthetic organic chemistry
    Volume
    2003
    Issue
    12
    DOI
    https://doi.org/10.1055/s-2003-41026
    Subject
    Organic Chemical Synthesis
    Analytical Chemistry
    Organic Chemistry
    Publication URI
    http://hdl.handle.net/10072/28188
    Collection
    • Journal articles

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