Cannabinoid compounds have captivated the interest of chemists for more than six decades.  The prospect of medicinal applications of cannabis for a vast array of ailments has inspired the isolation and characterization of more than one hundred small molecules from plant extracts.  Synthetic chemists have long been interested in efficient approaches to these natural products and their derivatives.  Herein we report a new gram scale synthesis of cannabigerol via the use of acidic alumina as an heterogeneous catalyst to perform direct allylation of olivetol with geraniol. Our allylation process constitutes significant improvements to previously reported Lewis Acid catalyzed methods.  Furthermore, we have expanded this chemistry to a generalized methodology for direct ortho-allylation of phenols which is applicable to the synthesis of various natural products including flavonoids.

Synthesis of Cannabigerol derivatives via direct <i>ortho</i>-allylation of phenols

2019 Fall National Meeting

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Synthesis of Cannabigerol derivatives via direct ortho-allylation of phenols