Functionalisation of artemisinin and its ring-contracted derivatives.
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 occurred diastereoselectively.
Van Neck
Tine
T
Department of Chemistry, University of Leuven, Celestijnenlaan 200F B-3001 Leuven, Belgium.
Van Mierloo
Sarah
S
Dehaen
Wim
W
D037621:Artemisinins / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D037621:Artemisinins; D006571:Heterocyclic Compounds; C031327:artemisinin