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Synthesis of 18 F‐labelled stilbenes from 4‐[ 18 F]fluorobenz‐aldehyde using the Horner–Wadsworth–Emmons reaction
Author(s) -
Gester Sven,
Pietzsch Jens,
Wuest Frank R.
Publication year - 2007
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.1172
Subject(s) - chemistry , aldehyde , high performance liquid chromatography , medicinal chemistry , organic chemistry , catalysis
The first application of the Horner–Wadsworth–Emmons reaction in 18 F‐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‐methoxy‐methoxybenzyl)‐phosphonic acid diethyl ester 3e and (4‐dimethyl‐aminobenzyl)phosphonic acid diethyl ester 4d ) with 4‐[ 18 F]fluorobenzaldehyde to give the corresponding 18 F‐labelled stilbenes [ 18 F]2g , [ 18 F]3g and [ 18 F]4e exclusively as the expected E ‐isomers. The radiochemical yields ranged from 9% to 22% (based upon [ 18 F]fluoride, including HPLC purification). The specific activity reached up to 90 GBq/µmol. Copyright © 2007 John Wiley & Sons, Ltd.