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

✍ Scribed by Sven Gester; Jens Pietzsch; Frank R. Wuest

Book ID
102368717
Publisher
John Wiley and Sons
Year
2007
Tongue
French
Weight
149 KB
Volume
50
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

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.

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