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The Deoxygenation and Isomerization of Artemisinin and Artemether and Their Relevance to Antimalarial Action

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Vicente, Maria G.H.
Millasson-Schmidt, Patricia
Published in Helvetica Chimica Acta. 1996, vol. 79, no. 5, p. 1475-1487
Abstract The treatment of artemisinin (1) and ß-artemether (6) with Zn dissolving in AcOH for a few hours results in mono-deoxygenation giving deoxyartemisinin (5) and deoxy-ß-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, (3aS,4R,6aS,7R,10S,10aR)-octahydro-4,7-dimethyl-8-oxo-2H-10H-furo[3,2-i] benzopyran-10-yl acetate (8) and (3R)-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.
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JEFFORD, Charles et al. The Deoxygenation and Isomerization of Artemisinin and Artemether and Their Relevance to Antimalarial Action. In: Helvetica Chimica Acta, 1996, vol. 79, n° 5, p. 1475-1487. https://archive-ouverte.unige.ch/unige:7823

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Deposited on : 2010-06-21

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