Construction of Spirofused Tricyclic Frameworks by NHC-Catalyzed Intramolecular Stetter Reaction of a Benzaldehyde Tether with a Cyclic Enone.

Various benzaldehyde tethers with a cyclic enone were prepared from commercially available 2-hydroxybenzaldehydes via a three-step sequence involving triflate formation, Sonogashira cross-coupling, and regioselective hydrogenation. These substrates were then exposed to an N-heterocyclic carbene, whereupon intramolecular Stetter reaction proceeded smoothly to give various spirofused tricyclic 1,4-diketones in 30-87% yields. Furaldehyde and nicotinaldehyde derivatives also participated in the reaction under the Stetter conditions.