A rearranged hydroperoxide from the reduction of artemisinin

Article abstract of DOI:10.1016/S0040-4020(97)00444-4

Lithium aluminium hydride reduction of artemisinin produces two unexpected rearrangement products in addition to those reported previously. The structure of the major rearrangement product, a tertiary hydroperoxide, was determined by 2D-NMR and chemical reactions. A mechanism is proposed for this rearrangement, based on the observation that dihydroartemisinin can also be converted into the same hydroperoxide in alkaline solution.