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  • Synthesis of antitrypanosomal 1,2-dioxane derivatives based on a natural product scaffold

    Author(s)
    Holla, Harish
    Labaied, Mehdi
    Ngoc, Pham
    Jenkins, Ian D
    Stuart, Kenneth
    Quinn, Ronald J
    Griffith University Author(s)
    Jenkins, Ian D.
    Quinn, Ronald J.
    Year published
    2011
    Metadata
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    Abstract
    A short practical synthesis of a new natural product based scaffold (6), based on antitrypanosomal and antimalarial compounds isolated from different Plakortis species is described. The scaffold contains a peroxide unit that is surprisingly stable to chemical manipulation elsewhere in the molecule, enabling it to be elaborated into a small library of derivatives. It is stable to ozonolysis, reductive work-up with dimethylsulfide and the Wittig reaction with stabilized phosphorus ylides. The scaffold along with its Wittig analogues has displayed low to sub-micro molar (0.2-3.3 lM) antitrypanosomal activity.A short practical synthesis of a new natural product based scaffold (6), based on antitrypanosomal and antimalarial compounds isolated from different Plakortis species is described. The scaffold contains a peroxide unit that is surprisingly stable to chemical manipulation elsewhere in the molecule, enabling it to be elaborated into a small library of derivatives. It is stable to ozonolysis, reductive work-up with dimethylsulfide and the Wittig reaction with stabilized phosphorus ylides. The scaffold along with its Wittig analogues has displayed low to sub-micro molar (0.2-3.3 lM) antitrypanosomal activity.
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    Journal Title
    Bioorganic & Medicinal Chemistry Letters
    Volume
    21
    Issue
    16
    DOI
    https://doi.org/10.1016/j.bmcl.2011.06.059
    Subject
    Medicinal and biomolecular chemistry
    Biologically active molecules
    Medicinal and biomolecular chemistry not elsewhere classified
    Organic chemistry
    Organic chemical synthesis
    Pharmacology and pharmaceutical sciences
    Publication URI
    http://hdl.handle.net/10072/40965
    Collection
    • Journal articles

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