The natural product bruceantin has long been studied for both its biological activity and its structural complexity. Attempts to synthesize more stable analogs for the development of inhibitors of γ-herpesviruses associated lymphomas are presented. In addition, a new method for the synthesis of the bridged bicyclic core structure of bruceantin using a homologous Pauson-Khand reaction of a bicyclo[2.1.0]pentane substrate is presented. Simple azabicyclo[2.1.0]pentane substrates were synthesized and studied for proof of concept of this approach in both rhodium- and palladium-catalyzed reactions. The palladium-mediated reaction led to the formation of enantiopure spirocyclic heterocycles.