Eur. J. Org. Chem. 2022, 26 (3), e202201226
DOI: 10.1002/ejoc.202201226
Dovhaniuk N.; Blahun O. P.; Sosunovych B.; Redka M. O.; Vashchenko B. V.; Grygorenko O. O.
A novel efficient method for the synthesis of licochalcone C in good yield on up to 30 g scale was developed. The reaction sequence included relied on the directed ortho-metalation (DOM) of bis-O-MOM-protected resorcinol for the regioselective C-prenylation, followed by metalation-formylation, selective O-deprotection of a hydroxyl group located between the formyl and prenyl groups, its methylation, and aldol reaction with p-hydroxyacetophenone. Synthesis of structurally related retrochalcones, i.e., licoagrochalcones B, C, and D, was also proposed.