Multicomponent Synthesis of 6H-Dibenzo[b,d]pyran-6-ones and a Total Synthesis of Cannabinol

A multicomponent domino reaction that affords 6H-dibenzo[b,d]pyran-6-ones Is reported. The overall transformation consists of six reactions: Knoevenagel condensation, transesterification, enamine formation, an inverse electron demand Diels-Alder (IEDDA) reaction, 1,2-elimination, and transfer hydrogenation. Both the diene and dienophile for the key inverse electron demand Diels-Alder (IEDDA) step are generated in situ by secondary amine-mediated processes. In most cases, the yields (10-79%) are considerably better than those obtained using a stepwise process. This methodology is employed In a concise total synthesis of cannabinol.