Synthesis of tachrosin, a natural flavone substituted by a novel furanoid ring system
Abstract
Tachrosin, 5,7-dimethoxy-8-( 2,3-dihydro-2,2-dimethyl-3-oxofuran-4-y1)flavone (1), was synthesised using the oxidative rearrangement of a 5-aryl-2-hydroxy-pent-4-en-3-one (2) with Tl(NO3)3 in methanol to a 4-aryl-5-methoxytetrahydrofuran-3-one (3) followed by elimination of the elements of methanol to form the dihydrofuranone ring.