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The reactivity of the anhydrodihydroartemisinin 2 and of its 10-trifluoromethyl analogue 3 toward brominating reagents was explored with the aim of preparing the new corresponding C-16 allylic bromides 5 and 7. Both glycals 2 and 3 react with NBS to provide compounds 5 and 7, respectively. From the 10-CF 3 anhydrodihydroartemisinin 3, the allylic bromination also occurred in high yield with...
Difluoroenoxysilanes, prepared from aromatic and heterocyclic ketones, reacted with dihydroartemisinin acetate in the presence of Lewis acid to provide in good to moderate yields the 10-substituted difluoromethylene ketones. The introduction of the difluoromethylketone moiety was accompanied by the epimerisation of C-9. Best results were obtained using SnCl 4 as Lewis acid.
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