1343474-00-9Relevant academic research and scientific papers
Multicomponent synthesis of 6 H-dibenzo[b,d]pyran-6-ones and a total synthesis of cannabinol
Nandaluru, Penchal Reddy,Bodwell, Graham J.
supporting information; experimental part, p. 310 - 313 (2012/02/04)
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.
