Expedient synthesis of an atypical oxazolidinone compound library

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

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)
9 Downloads (Pure)

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.
Original languageEnglish
Pages (from-to)5249-5257
Number of pages9
JournalBioorganic & Medicinal Chemistry
Volume24
Issue number21
Early online date27 Aug 2016
DOIs
Publication statusPublished - 1 Nov 2016

Keywords

  • sp3-rich
  • Library
  • Bicyclic
  • Scaffold
  • Oxazolidinone

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