Ballerini E, Minuti L, Piermatti O, Pizzo F
High Pressure Diels-Alder Approach to Hydroxy-Substituted 6a-Cyano-tetrahydro-6H-benzo[c]chromen-6-ones: A Route to Delta(6)-Cis-Cannabidiol. [JOURNAL ARTICLE]
J Org Chem 2009 Apr 29.
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 Delta(6)-3,4-cis-cannabidiol (Delta(6)-cis-CBD) and Delta(8)-cis-tetrahydrocannabinol (Delta(8)-cis-THC) is outlined.
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