Abstract
The one-pot conversion of ajmaline 1 into the nitrile 4 (X-ray structure) and suaveoline 2a is reported; both reactions utilise hydroxylamine hydrochloride in a refluxing alcohol, and involve unusual multi-step mechanisms in which the product ratio can be controlled by the choice of the alcohol. In an additional unusual oxidation, the synthetic intermediate 14 used in a synthesis of suaveoline can be oxidatively cyclized to 16.
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