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Molecules 2007, 12(3), 395-405; doi:10.3390/12030395
Article

Functionalisation of Artemisinin and Its Ring-contracted Derivatives

,  and *
Department of Chemistry, University of Leuven, Celestijnenlaan 200F B-3001 Leuven, Belgium
* Author to whom correspondence should be addressed.
Received: 1 March 2007 / Revised: 8 March 2007 / Accepted: 8 March 2007 / Published: 9 March 2007
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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 Artemisinin; ring contraction; aldehyde; 1; 3-dipolar cycloaddition; nitrile oxide
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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