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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...
The Swern oxidation of various indolic substrates is described, and a range of products resulting from overalloxidation at the 2-position were observed. In particular, depending on the substrate and reaction conditions, it was possible to achieve direct oxidation to α,β-unsaturated systems at the 2-position, to introduce a nucleophile at the 2-position, and to introduce a CH 3 -S-CH 2...
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