Synthesis of the ABC Core of Daphniphyllum Alkaloids with a [5-6-7] Azatricyclic Scaffold via Ring Expansion of Azabicyclic and Azatricyclic Building Blocks.

Abstract

The [5-6-7] azatricyclic ABC core, found in several Daphniphyllum alkaloids, has been synthesized through a novel route involving ring expansion of a perhydroindolone to afford the AC ring system and a radical B ring closure as key steps. The level of functionalization of the reported octahydro-1,7-ethanocyclohepta[b]pyrroles suggests that they can serve as valuable building blocks in this alkaloid field. Also reported is the first synthesis of homomorphans by the ring enlargement of 2-azabicyclo[3.3.1]nonanes.