title: Diastereoselective synthesis of 3-acetoxy-4-(3-aryloxiran-2-yl)azetidin-2-ones and their transformation into 3,4-oxolane-fused bicyclic β-lactams.
abstract: cis-3-Acetoxy-4-(3-aryloxiran-2-yl)azetidin-2-ones were prepared through a Staudinger [2+2]-cyclocondensation between acetoxyketene and the appropriate epoxyimines in a highly diastereoselective way. Subsequent potassium carbonate-mediated acetate hydrolysis, followed by intramolecular ring closure through epoxide ring opening, afforded stereodefined 3-aryl-4-hydroxy-2-oxa-6-azabicyclo[3.2.0]heptan-7-ones as a novel class of C-fused bicyclic β-lactams. Selective benzylic oxidation of bicyclic N-(4-methoxybenzyl)-β-lactams with potassium persulfate and potassium dihydrogen phosphate provided the corresponding N-aroyl derivatives as interesting leads for further β-lactamase inhibitor development.
authors.affiliation: SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium. matthias.dhooghe@UGent.be.
authors.forename: Nicola
authors.initials: N
authors.lastname: Piens
authors.affiliation: SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium. matthias.dhooghe@UGent.be.
authors.forename: Sven
authors.initials: S
authors.lastname: De Craene
authors.affiliation: Department of Biochemical and Microbial Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Jorick
authors.initials: J
authors.lastname: Franceus
authors.affiliation: SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium. matthias.dhooghe@UGent.be.
authors.forename: Karen
authors.initials: K
authors.lastname: Mollet
authors.affiliation: XStruct, Department of Inorganic and Physical Chemistry, Faculty of Sciences, Ghent University, Krijgslaan 281-S3, B-9000 Ghent, Belgium.
authors.forename: Kristof
authors.initials: K
authors.lastname: Van Hecke
authors.affiliation: Department of Biochemical and Microbial Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Tom
authors.initials: T
authors.lastname: Desmet
authors.affiliation: SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium. matthias.dhooghe@UGent.be.
authors.forename: Matthias
authors.initials: M
authors.lastname: D'hooghe
mesh_terms: D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D015195:Drug Design; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism; D047090:beta-Lactams / Q000737:chemistry*
chemical_list: D001384:Azetidines; D047090:beta-Lactams; C082735:azetidine