title: Uncatalysed diaryldiazo cyclopropanations on bicyclic lactams: access to annulated prolines.
abstract: The uncatalysed cycloaddition of substituted diaryldiazo compounds onto bicyclic unsaturated lactams derived from pyroglutamic acid efficiently leads to highly functionalised azatricyclononanes. The products are readily elaborated to deprotected pyroglutamate derivatives, providing rapid access to conformationally constrained amino acids and their analogues. Preliminary assessment of antibacterial activity against one Gram positive and one Gram negative organism indicated high levels of efficacy in some cases.
authors.affiliation: The Department of Chemistry, Chemistry Research Laboratory, The University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK. mark.moloney@chem.ox.ac.uk.
authors.forename: Lawrence
authors.initials: L
authors.lastname: Harris
authors.forename: Martin
authors.initials: M
authors.lastname: Gilpin
authors.forename: Amber L
authors.initials: AL
authors.lastname: Thompson
authors.forename: Andrew R
authors.initials: AR
authors.lastname: Cowley
authors.forename: Mark G
authors.initials: MG
authors.lastname: Moloney
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D003521:Cyclopropanes / Q000737:chemistry; D004353:Drug Evaluation, Preclinical / Q000379:methods; D004926:Escherichia coli / Q000187:drug effects; D007769:Lactams / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011392:Proline / Q000737:chemistry; D011761:Pyrrolidonecarboxylic Acid / Q000737:chemistry; D013211:Staphylococcus aureus / Q000187:drug effects
chemical_list: D000900:Anti-Bacterial Agents; D003521:Cyclopropanes; D007769:Lactams; C030797:cyclopropane; D011392:Proline; D011761:Pyrrolidonecarboxylic Acid