Expedient synthesis of an atypical oxazolidinone compound library. Issue 21 (1st November 2016)

• Record Type: Journal Article
• Authors: 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.
• Is Part Of: Bioorganic & medicinal chemistry. Volume 24:Issue 21(2016)
• Page Start: 5249
• Page End: 5257
• Publication Date: 2016-11-01
• Subjects: sp3-rich -- Library -- Bicyclic -- Scaffold -- Oxazolidinone; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2016.08.046
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Abstract: In order to address the current downturn in the drug discovery pipeline, initiatives are being undertaken to synthesise screening libraries of sp 3 -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(1 H )-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.