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. 2014 Feb;57(2):102-3.
doi: 10.1002/jlcr.3172. Epub 2014 Jan 10.

Synthesis of [7-(14) C]bergapten

Crist N Filer  1 , Thomas Rodgers
Affiliations

Synthesis of [7-(14) C]bergapten

Crist N Filer et al. J Labelled Comp Radiopharm. 2014 Feb.

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.

Keywords: Bergapten; Wittig reaction; carbon-14; furocoumarin.

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