Synthesis of flavonoid-type compounds from methyl dehydroabietates

Abstract

The synthesis of new flavone-type compounds bearing several chiral centres, 12- and 14-(2'-chromonyl)dehydroabietates, are reported. This synthesis started from the aldol condensation of methyl 12- and 14-formyldehydroabietates with 2'-hydroxyacetophenones in order to prepare the corresponding chalcone-type compounds, which were then transformed in the expected flavone-type compounds by cyclodehydrogenation with DMSO and a catalytic amount of iodine. All compounds were exhaustively characterised by NMR and MS techniques.