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Synthesis of carbon‐14 labelled (5 Z )‐4‐bromo‐5‐(bromomethylene)‐2(5 H )‐furanone: a potent quorum sensing inhibitor
Author(s) -
Persson Tobias,
Johansen Steen K.,
Martiny Lars,
Givskov Michael,
Nielsen John
Publication year - 2004
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.846
Subject(s) - chemistry , yield (engineering) , decarboxylation , levulinic acid , halogenation , ethyl acetoacetate , acetic acid , furan , organic chemistry , medicinal chemistry , nuclear chemistry , stereochemistry , catalysis , materials science , metallurgy
The potent quorum sensing inhibitor (5 Z )‐4‐bromo‐5‐(bromomethylene)‐2(5 H )‐[2‐ 14 C]furanone has been prepared in five steps in 7.7% overall yield starting from bromo[1‐ 14 C]acetic acid. Condensation of ethyl bromo[1‐ 14 C]acetate with ethyl acetoacetate followed by decarboxylation was accelerated by microwave heating to afford [1‐ 14 C]levulinic acid. Subsequently, bromination and oxidation gave the targeted furan‐2‐one with a radiochemical purity of > 97% and a specific activity of 57 mCi/mmol. Copyright © 2004 John Wiley & Sons, Ltd.