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

T. Persson; S.K. Johansen; L. Martiny; Michael Christian Givskov; J. Nielsen

doi:10.1002/jlcr.846

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

T. Persson, S.K. Johansen, L. Martiny, Michael Christian Givskov, J. Nielsen

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

The potent quorum sensing inhibitor (5Z)-4-bromo-5-(bromomethylene)-2(5H)-[2-C-14]furanone has been prepared in five steps in 7.7% overall yield starting from bromo[1-C-14]acetic acid. Condensation of ethyl bromo[1-C-14]acetate with ethyl acetoacetate followed by decarboxylation was accelerated by microwave heating to afford [1-C-14]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.

Original language	English
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	47
Issue number	10
Pages (from-to)	627-634
ISSN	0362-4803
DOIs	https://doi.org/10.1002/jlcr.846
Publication status	Published - 2004

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

abstract = "The potent quorum sensing inhibitor (5Z)-4-bromo-5-(bromomethylene)-2(5H)-[2-C-14]furanone has been prepared in five steps in 7.7% overall yield starting from bromo[1-C-14]acetic acid. Condensation of ethyl bromo[1-C-14]acetate with ethyl acetoacetate followed by decarboxylation was accelerated by microwave heating to afford [1-C-14]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.",

author = "T. Persson and S.K. Johansen and L. Martiny and Givskov, {Michael Christian} and J. Nielsen",

year = "2004",

doi = "10.1002/jlcr.846",

language = "English",

volume = "47",

pages = "627--634",

journal = "Journal of Labelled Compounds and Radiopharmaceuticals",

issn = "0362-4803",

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T1 - Synthesis of carbon-14 labelled (5Z)-4-bromo-5-(bromomethylene)-2(5H)-furanone:

T2 - a potent quorum sensing inhibitor

AU - Persson, T.

AU - Johansen, S.K.

AU - Martiny, L.

AU - Givskov, Michael Christian

AU - Nielsen, J.

PY - 2004

Y1 - 2004

N2 - The potent quorum sensing inhibitor (5Z)-4-bromo-5-(bromomethylene)-2(5H)-[2-C-14]furanone has been prepared in five steps in 7.7% overall yield starting from bromo[1-C-14]acetic acid. Condensation of ethyl bromo[1-C-14]acetate with ethyl acetoacetate followed by decarboxylation was accelerated by microwave heating to afford [1-C-14]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.

AB - The potent quorum sensing inhibitor (5Z)-4-bromo-5-(bromomethylene)-2(5H)-[2-C-14]furanone has been prepared in five steps in 7.7% overall yield starting from bromo[1-C-14]acetic acid. Condensation of ethyl bromo[1-C-14]acetate with ethyl acetoacetate followed by decarboxylation was accelerated by microwave heating to afford [1-C-14]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.

U2 - 10.1002/jlcr.846

DO - 10.1002/jlcr.846

M3 - Journal article

SN - 0362-4803

VL - 47

SP - 627

EP - 634

JO - Journal of Labelled Compounds and Radiopharmaceuticals

JF - Journal of Labelled Compounds and Radiopharmaceuticals

IS - 10

ER -

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

Abstract

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