Synthesis of antitrypanosomal 1,2-dioxane derivatives based on a natural product scaffold
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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.
Bioorganic & Medicinal Chemistry Letters
Organic Chemical Synthesis
Biologically Active Molecules
Medicinal and Biomolecular Chemistry not elsewhere classified