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Berberine is a widely used antimicrobial agent in clinic. However, a high dosage is often required due to its low lipophilicity and bioavailability. The current study explores the structural modifications of berberines with potentially lipophilic aryl groups to address this problem. A series of 15 9-O-aryl-substituted berberines ( 3a - o ) and one 9-O-phenylene-bridged berberine dimer ( 5 ) was synthesized by copper-catalyzed cross-coupling of tetrahydroberberrubine and aryl iodides, followed by oxidation with I 2 .

Synthesis of 9-O-arylated berberines via copper-catalyzed CAr–O coupling reactions

Synthesis of 9-O-arylated berberines via copper-catalyzed C_Ar–O coupling reactions