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High Pressure Diels−Alder Approach to Hydroxy-Substituted 6a-Cyano-tetrahydro-6H-benzo[c]chromen-6-ones: A Route to Δ6-Cis-Cannabidiol

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journal contribution
posted on 05.06.2009, 00:00 by Eleonora Ballerini, Lucio Minuti, Oriana Piermatti, Ferdinando Pizzo
Diels−Alder cycloaddition reactions of 3-cyanocoumarin, hydroxy-substituted 3-cyanocoumarins and mesyl-substituted 3-cyano-coumarins with methyl-1,3-butadienes carried out under high pressure (11 kbar) are reported. Activation by high pressure allows these reactions to proceed satisfactorily under mild conditions to produce 6a-cyano-hydroxy- and 6a-cyano-mesyl-tetrahydro-6H-benzo[c]chromen-6-ones in moderate to excellent yield. The synthesis of cis-1-hydroxy-9-methyl-3-pentyl-6a,7,10,10a-tetrahydro-benzo[c]chromen-6-one as precursor of Δ6-3,4-cis-cannabidiol (Δ6-cis-CBD) and Δ8-cis-tetrahydrocannabinol (Δ8-cis-THC) is outlined.