Journal of Organic Chemistry 2012-09-21

High-pressure-promoted Diels-Alder approach to biaryls: application to the synthesis of the cannabinols family.

Lucio Minuti, Andrea Temperini, Eleonora Ballerini

Index: J. Org. Chem. 77(18) , 7923-31, (2012)

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Abstract

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 cyclohexadienyl-benzene 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.