Studies towards the synthesis of montamine: synthesis of the 1,2-bis(indolyl)ethylhydrazine fragment

The synthesis of a protected 1,2-bis(indolyl)ethylhydrazine bearing the full substitution pattern present in the unusual dimeric alkaloid montamine is described. A variant of the Mitsunobu reaction was used to incorporate directly the reduced azodicarboxylate into the tryptophol side chain. The resulting carbazate underwent alkylation to give the core structure of the natural product. (C) 2013 Elsevier Ltd. All rights reserved.