Functionalisation of Artemisinin and Its Ring-contracted Derivatives

doi:10.3390/12030395

This article is

freely available
re-usable

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

Article

Functionalisation of Artemisinin and Its Ring-contracted Derivatives

Tine Van Neck, Sarah Van Mierloo and Wim Dehaen*

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

Download PDF Full-Text [99 KB, uploaded 20 June 2008 16:50 CEST]

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

Article Statistics

Click here to load and display the download statistics.

Cite This Article

MDPI and ACS Style

Van Neck, T.; Van Mierloo, S.; Dehaen, W. Functionalisation of Artemisinin and Its Ring-contracted Derivatives. Molecules 2007, 12, 395-405.

AMA Style

Van Neck T, Van Mierloo S, Dehaen W. Functionalisation of Artemisinin and Its Ring-contracted Derivatives. Molecules. 2007; 12(3):395-405.

Chicago/Turabian Style

Van Neck, Tine; Van Mierloo, Sarah; Dehaen, Wim. 2007. "Functionalisation of Artemisinin and Its Ring-contracted Derivatives." Molecules 12, no. 3: 395-405.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert