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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]

PMID: 21757346

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