Magnesium dicarboxylates promote the prenylation of phenolics that is extended to the total synthesis of icaritin
Jichao Zhang, Wei Xiong, Yongju Wen, Xuewen Fu, Xiaoxia Lü, Guolin Zhang, Chun Wang
Abstract
-products. Mechanistic study of the prenylation provided evidence for the nucleophilic addition/substitution of the phenolic substrate to the alkyl halide in the presence of the magnesium dicarboxylates. The proto application of this method in the total synthesis of icaritin through the prenylation of 2,4,6-trihydroxyacetophenone, followed by the reaction with benzaldehyde to afford the flavonol, was successful, with a total yield of 33%.
Topics & Concepts
ChemistryPrenylationYield (engineering)MagnesiumSolventSelectivitySubstrate (aquarium)Medicinal chemistryOrganic chemistryStereochemistryCatalysisMaterials scienceOceanographyMetallurgyGeologyEnzymeMedicinal Plant Pharmacodynamics ResearchPhytochemical compounds biological activitiesNatural product bioactivities and synthesis