Efficient Synthesis of Cannabigerol, Grifolin, and Piperogalin via Alumina-Promoted Allylation
Nicholas G. Jentsch, Xiong Zhang, Jakob Magolan
Abstract
The synthesis of three phenolic natural products has been accomplished with unprecedented efficiency using a new alumina-promoted regioselective aromatic allylation reaction. Cannabigerol and grifolin were prepared in one step from the inexpensive 5-alkyl-resorcinols olivetol and orcinol. Piperogalin was synthesized, for the first time, via two sequential allylations of orcinol with geraniol and prenol.
Topics & Concepts
OrcinolGeraniolRegioselectivityChemistryOrganic chemistryAlkylPhenolsCombinatorial chemistryCatalysisChromatographyEssential oilBioactive natural compoundsTraditional and Medicinal Uses of AnnonaceaeAlkaloids: synthesis and pharmacology