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- Title
The Deoxygenation and Isomerization of Artemisinin and Artemether and Their Relevance to Antimalarial Action.
- Authors
Jefford, Charles W.; Vicente, Maria G. H.; Jacquier, Yvan; Favarger, France; Mareda, Jiri; Millasson-Schmidt, Patricia; Brunner, Gerhard; Burger, Ulrich
- Abstract
The treatment of artemisinin ( 1) and β-artemether ( 6) with Zn dissolving in AcOH for a few hours results in mono-deoxygenation giving deoxyartemisinin ( 5) and deoxy-β-artemether ( 7), respectively, as the sole product. In contrast, submission of 1 to FeCl2 · 4 H2O in MeCN at room temperature for 15 min causes only isomerization, (3a S,4 R,6a S,7 R,10 S,10a R)-octahydro-4,7-dimethyl-8-oxo-2 H-10 H-furo[3,2- i] benzopyran-10-yl acetate ( 8) and (3 R)-3-hydroxydeoxyartemisinin ( 9) being produced in 78 and 17% yield, respectively. The action of FeCl2 · 4 H2O in MeCN on 6 is similar. Under the same conditions, 6 gives products analogous to 8 and 9 accompanied by an epimeric mixture of 2-[4-methyl-2-oxo-3-(3-oxobutyl)cyclohexyl]propanaldehyde in yields of 32, 23, and 16%, respectively. No epoxide is formed on repeating the last two experiments in the presence of cyclohexene. The deoxygenation of 1 and 6 by Zn is rationalized in terms of its oxophilic nature. The catalyzed isomerization of 1 and 6 by Fe2+ is attributed to the redox properties of the Fe2+/Fe3+ system.
- Publication
Helvetica Chimica Acta, 1996, Vol 79, Issue 5, p1475
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19960790520