Synthesis of a New Naturally Occurring 3-Phenyl-4H-1-Benzopyran-4-One

7-Hydroxy-8-methoxy-3-(3,4-methylenedioxyphenyl)-4H-1-benzopyran-4-one (1), a new isoflavone reported to occur in the aerial parts and roots of Tephrosia maxima has been synthesized by the oxidative rearrangement of 2′-hydroxy-3′-methoxy-4′-benzyloxy-3,4-methylenedioxychalcone (4) with thallium (III) nitrate (TTN) in trimethyl orthoformate (TMOF), followed by acid catalysed cyclization and debenzylation. It has also been synthesized by another method from 2,3,4-trihydroxy-3,4′-methylenedioxydeoxybenzoin; the hitherto unknown biisoflavone, 7,7′-dimethoxy-3′,4″,3″,4″-dimethylenedioxy-8,8′-biisoflavonyl ether was also formed during this method.