Synthesis of Deuterium Labeled Polyhydroxy Flavones and 3-Flavonols

Syntheses are described for seven new deuterium labeled flavones, [3,6,8,3′,5′-D5]-apigenin 5, [3,3′,5′-D3]-apigenin 6, [3,6,8,2′,5′,6′-D6]-luteolin 7, [3,2′,5′,6′-D4]-luteolin 8, [6,8,2′,5′,6′-D5]-quercetin 9, [2′,5′,6′-D3]-quercetin 10 and [8,2′,5′,6′-D4]-fisetin 11, using D3PO4·BF3/D2O as a deuteration reagent. The products were characterized by NMR and mass spectrometry.