Expedient synthesis of an atypical oxazolidinone compound library
Cully, Sarah J. and Storr, Thomas E. and Rawling, Michael J. and Abeysena, Induka R. and Hamza, Daniel and Jones, Geraint and Pearce, Christopher A. and Quddus, Abdul and Lewis, William and Stockman, Robert A. (2016) Expedient synthesis of an atypical oxazolidinone compound library. Bioorganic and Medicinal Chemistry . ISSN 1464-3391
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.
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