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Functionalisation of Artemisinin and Its Ring-contracted Derivatives
Department of Chemistry, University of Leuven, Celestijnenlaan 200F B-3001 Leuven, Belgium
* Author to whom correspondence should be addressed.
Received: 1 March 2007; in revised form: 8 March 2007 / Accepted: 8 March 2007 / Published: 9 March 2007
Abstract: Isoxazoline analogues of artemisinin were obtained in low yield and low diastereoselectivity from the 1,3-dipolar cycloaddition of nitrile oxides. Alternatively, starting from the aldehyde 7, a number of transformations - Wittig reaction and reduction, Henry reaction and cyanohydrin formation - were achieved in significantly higher yields. In the cases where a new stereocenter was introduced this occured diastereoselectively.
Keywords: Artemisinin; ring contraction; aldehyde; 1; 3-dipolar cycloaddition; nitrile oxide
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Van Neck, T.; Van Mierloo, S.; Dehaen, W. Functionalisation of Artemisinin and Its Ring-contracted Derivatives. Molecules 2007, 12, 395-405.
Van Neck T, Van Mierloo S, Dehaen W. Functionalisation of Artemisinin and Its Ring-contracted Derivatives. Molecules. 2007; 12(3):395-405.
Van Neck, Tine; Van Mierloo, Sarah; Dehaen, Wim. 2007. "Functionalisation of Artemisinin and Its Ring-contracted Derivatives." Molecules 12, no. 3: 395-405.