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Synthesis of [7‐ 14 C]bergapten
Author(s) -
Filer Crist N.,
Rodgers Thomas
Publication year - 2014
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3172
Subject(s) - chemistry , bergapten , radiochemistry , biochemistry , psoralen , dna
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.

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