Synthesis of [7‐14C]bergapten. (10th January 2014) - Filer, Crist N.
Abstract Bergapten (1) is a furocoumarin natural product and currently employed to treat skin disorders. Since past attempts to radiolabel 1 with 14C were limited to only its 5‐methoxy group, a synthesis of the required ring [7‐14C]1 is now described. The literature reported precursor 4‐methoxy‐6‐hydroxybenzofuran‐5‐carboxaldehyde (3) was Wittig reacted with stabilized [carbonyl‐14C]methoxycarbonylmethylenetriphenylphosphorane (4) to obtain [7‐14C]1 in 47% radiochemical yield, with the desired product being characterized by thin‐layer chromatography, HPLC, m.p. and proton NMR.