title: Synthesis of [7-(14) C]bergapten.
abstract: Bergapten (1) is a furocoumarin natural product and currently employed to treat skin disorders. Since past attempts to radiolabel 1 with (14) C were limited to only its 5-methoxy group, a synthesis of the required ring [7-(14) C]1 is now described. The literature reported precursor 4-methoxy-6-hydroxybenzofuran-5-carboxaldehyde (3) was Wittig reacted with stabilized [carbonyl-(14) C]methoxycarbonylmethylenetriphenylphosphorane (4) to obtain [7-(14) C]1 in 47% radiochemical yield, with the desired product being characterized by thin-layer chromatography, HPLC, m.p. and proton NMR.
authors.affiliation: PerkinElmer Life Sciences & Technology Inc., 940 Winter Street, Waltham, MA, 02451, USA.
authors.forename: Crist N
authors.initials: CN
authors.lastname: Filer
authors.forename: Thomas
authors.initials: T
authors.lastname: Rodgers
mesh_terms: D000078223:5-Methoxypsoralen; D002250:Carbon Radioisotopes / Q000737:chemistry; D007553:Isotope Labeling; D008730:Methoxsalen / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D002250:Carbon Radioisotopes; D000078223:5-Methoxypsoralen; D008730:Methoxsalen
keywords: Bergapten; Wittig reaction; carbon-14; furocoumarin