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Synthesis of 18F-labelled stilbenes from 4-[18F]fluorobenzaldehyde using the Horner-Wadsworth-Emmons reaction

Gester, S.; Pietzsch, J.; Wüst, F.
The first application of the Horner-Wadsworth-Emmons reaction in 18F-chemistry is described. This carbonyl-olefination reaction was performed via a “multi-step/one-pot” reaction by the coupling of benzylic phosphonic acid esters (3,5-bis-methoxymethoxybenzyl)-phosphonic acid diethyl ester 2e, (4-methoxymethoxybenzyl)-phosphonic acid diethyl ester 3e and (4-dimethyl-aminobenzyl)phosphonic acid diethyl ester 4d) with 4-[18F]fluorobenzaldehyde to give the corresponding 18F-labelled stilbenes [18F]2g, [18F]3g and [18F]4e exclusively as the expected E-isomers. The radiochemical yields ranged from 9 to 22% (based upon [18F]fluoride, including HPLC purification). The specific activity reached up to 90 GBq/µmol.
Keywords: 18F-labelled stilbenes; [18F]fluorobenzaldehyde; Horner-Wadsworth-Emmons reaction
  • Journal of Labelled Compounds and Radiopharmaceuticals 50(2007)2, 105-113
    DOI: 10.1002/jlcr.1172

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Publ.-Id: 8955