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Synthesis of carbon-14 labelled (5Z)-4-bromo-5-(bromomethylene)-2(5H)-furanone: a potent quorum sensing inhibitor

✍ Scribed by Tobias Persson; Steen K. Johansen; Lars Martiny; Michael Givskov; John Nielsen

Publisher: John Wiley and Sons
Year: 2004
Tongue: French
Weight: 105 KB
Volume: 47
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.846

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✦ Synopsis

Abstract

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.

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