Synthesis of isoflavonoid deuterium labeled polyphenolic Phytoestrogens

Article abstract of DOI:10.1016/S0040-4020(98)01153-3

Deuteration methods are described for the synthesis of new stable deuterium labeled isoflavonoids, [8,3',5'-D₃]-daidzein 4a, [8,3',5'-D₃]- formononetin 4b, [2',3',5',6'-D₄]-biochanin A 4c, [6,8,3',5'- D₄]dihydrodaidzein 5a, [3,6,8,3',5'-D₅]-dihydrodaidzein 5b, [3,2',3',5',6'- D₅]-dihydrogenistein 5c and [2,4,8,10-D₄]-coumestrol 6, using D₃PO₄·BF₃/D₂O as a deuteration reagent. Positions of deuterium labels and isotopic purities were determined by NMR and mass spectrometry. The relative of H/D exchange at the various aromatic sites is discussed.