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

Persson Tobias | Zendy; Johansen Steen K. | Zendy; Martiny Lars | Zendy; Givskov Michael | Zendy; Nielsen John | Zendy

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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.

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