Abstract
The bromination and oxidation of securinine were studied. An interesting and surprising rearrangement was observed during the reaction of securinine with tribromo-isocyanuric acid or 1,3-dibromo-5,5-dimethylhydantoin in methanol, yielding a stereoselective ring contraction norsecurinine derivative. Meanwhile two oxidation rearrangement products were also reported. Some preliminary discussions on the reactivity of securinine were conducted from these rearrangements; it is believed to be induced by alkaline nitrogen atom of the molecule.
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