Sarah J. Cully
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
Thomas E. Storr
Michael J. Rawling
Induka R. Abeysena
Daniel Hamza
Geraint Jones
Christopher A. Pearce
Abdul Quddus
William Lewis
ROBERT STOCKMAN robert.stockman@nottingham.ac.uk
Professor of Organic Chemistry
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 | https://nottingham-repository.worktribe.com/output/804261 |
Publisher URL | http://www.sciencedirect.com/science/article/pii/S096808961630654X |
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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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