Abstract
AbstractThe 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, (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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