Synthese von natürlichen Haloindolen via Hetero-Cope-Umlagerung von Vinyl-N-phenylhydroxamaten

Synthesis of Natural, Halogenated Indoles via Hetero-Cope Rearrangement of Vinyl N-Phenylhydroxamates An efficient method for the synthesis of natural 4-chloro-6-methoxyindole (the promutagen from fava beans) and of the two 4,6- dibromo- and 3,4,6-tribromoindoles (produced by acorn worms, Enteropneusta) is presented. The key step is a hetero-Cope rearrangement of the intermediate N-phenyl-O-vinylhydroxylamine derivatives.