High-Pressure-Promoted Diels–Alder Approach to Biaryls: Application to the Synthesis of the Cannabinols Family

Diels - Alder reactions of a range of 1-(alkoxy/alkyl/halogen-substituted phenyl)buta-1,3-dienes with methyl propiolate carried out in a green ethanolic medium under 9 kbar pressure were investigated. The use of high pressure as activating method of the Diels - Alder reactions allows efficient and regioselective generation of a series of cyclohexadienylbenzene cycloadducts that are oxidized to the corresponding biaryls. The alkoxy/alkyl/halogen- substituted biaryls produced are useful precursors for accessing substituted 6H-benzo[c]chromen-6-ones and the cannabinols family. © 2012 American Chemical Society.