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Expedient synthesis of an atypical oxazolidinone compound library

Cully, Sarah J.; Storr, Thomas E.; Rawling, Michael J.; Abeysena, Induka R.; Hamza, Daniel; Jones, Geraint; Pearce, Christopher A.; Quddus, Abdul; Lewis, William; Stockman, Robert A.

Authors

Sarah J. Cully

Thomas E. Storr

Michael J. Rawling

Induka R. Abeysena

Daniel Hamza

Geraint Jones

Christopher A. Pearce

Abdul Quddus

William Lewis



Abstract

In order to address the current downturn in the drug discovery pipeline, initiatives are being undertaken to synthesise screening libraries of sp3-rich, low molecular weight compounds. As part of the European Lead Factory initiative, the synthesis and derivatisation of a simple hexahydrooxazolo[5,4-c]pyridin-2(1H)-one bicyclic carbamate has been achieved. The synthetic route employed involved a telescoped hetero-Diels-Alder/[2,3]-sigmatropic rearrangement/cyclisation sequence to deliver the desired core scaffold containing two points for further diversification. When applied, this synthesis was found to be robust and scalable which allowed the production of a 155 compound library.

Citation

Cully, S. J., Storr, T. E., Rawling, M. J., Abeysena, I. R., Hamza, D., Jones, G., …Stockman, R. A. (2016). Expedient synthesis of an atypical oxazolidinone compound library. Bioorganic and Medicinal Chemistry, 24(21), 5249-5257. https://doi.org/10.1016/j.bmc.2016.08.046

Journal Article Type Article
Acceptance Date Aug 25, 2016
Online Publication Date Aug 27, 2016
Publication Date Nov 1, 2016
Deposit Date Sep 1, 2016
Publicly Available Date Sep 1, 2016
Journal Bioorganic and Medicinal Chemistry
Print ISSN 0968-0896
Electronic ISSN 1464-3391
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 24
Issue 21
Pages 5249-5257
DOI https://doi.org/10.1016/j.bmc.2016.08.046
Public URL http://eprints.nottingham.ac.uk/id/eprint/36176
Publisher URL http://www.sciencedirect.com/science/article/pii/S096808961630654X
Copyright Statement Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by-nc-nd/4.0

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by-nc-nd/4.0





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