Palladium-Catalyzed Syntheses of Indoles (Paperback)

A variety of heterocyclic compounds including indoles, quinolines, and pyrroloindoles has been synthesized. The key step in these alkaloids' syntheses is a palladium-catalyzed reductive N-heteroannulation previously discovered in our laboratory. The ultimate reducing agent in these palladium-catalyzed cyclizations is carbon monoxide. Furthermore, a base-mediated formation of 2-unsubstituted N-alkoxyindoles is described from readily available nitrostyrenes. Finally, progress towards the first total synthesis of the highly bioactive Echinosulfone A is reported.