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

Synthesis of [7-(14) C]bergapten.

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  • 1PerkinElmer Life Sciences & Technology Inc., 940 Winter Street, Waltham, MA, 02451, USA.


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.

Copyright © 2014 John Wiley & Sons, Ltd.


Bergapten; Wittig reaction; carbon-14; furocoumarin

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