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


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 ?M) antitrypanosomal activity.

SUBMITTER: Holla H 

PROVIDER: S-EPMC3228865 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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

Holla Harish H   Labaied Mehdi M   Pham Ngoc N   Jenkins Ian D ID   Stuart Kenneth K   Quinn Ronald J RJ  

Bioorganic & medicinal chemistry letters 20110713 16


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 scaf  ...[more]

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