Abstract
A general and single step synthesis of polyhydroxydihydrochalcones from the readily available phenols and dihydrocinnamic acids using BF 3·Et 2O is described. The method allows the synthesis of a wide range of compounds with multiple phenolic hydroxyls and other substituents. These dihydrochalcones are converted into homoisoflavonoids by DMF/PCl 5 and the methodology has been applied to the synthesis of naturally occurring phloretin and 5,7-dihydroxy-3-[(4-hydroxyphenyl)methyl]-4 H-chromen-4-one. The antioxidant activity of dihydrochalcones and homoisoflavonoids was determined by superoxide free radical (NBT) and DPPH free radical scavenging methods. Polyhydroxydihydrochalcones 3c , 3f , 3g and homoisoflavonoids 4c , 4f , 4g displayed excellent antioxidant activity.
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