Synthesis of Strained γ-Lactams by Palladium(0)-Catalyzed C(sp(3) )-H Alkenylation and Application to Alkaloid Synthesis

Abstract

A variety of strained α-alkylidene-γ-lactams were synthesized by palladium(0)-catalyzed intramolecular C(sp(3) )-H alkenylation from easily accessible acyclic and monocyclic bromoalkene precursors. These lactams are valuable intermediates for accessing various classes of mono- and bicylic alkaloids containing a pyrrolidine ring, as illustrated with the synthesis of an advanced model of the marine natural product plakoridine A and of the indolizidine alkaloid δ-coniceine.

Keywords: C−C coupling; C−H activation; natural products; nitrogen heterocycles; palladium.