title: Synthesis of 2-fluoro-6-O-propargyl-11,12-carbamate ketolides. A novel class of antibiotics.
abstract: A novel class of 2-fluoro-6-O-propargyl-11,12-carbamate ketolide derivatives of erythromycin has been synthesized for antibacterial SAR studies. Replacement of the C2-hydrogen by a fluorine atom allows the synthesis of 6-O-propargylic ketones and electron-deficient 6-O-propargylic aromatic derivatives by preventing intramolecular C2-enolate Michael cyclization.
authors.affiliation: Infectious Diseases Research, Abbott Laboratories, 200 Abbott Park Road, Abbott Park, Illinois 60064-3537, USA. ly.phan@abbott.com
authors.forename: L T
authors.initials: LT
authors.lastname: Phan
authors.forename: R F
authors.initials: RF
authors.lastname: Clark
authors.forename: M
authors.initials: M
authors.lastname: Rupp
authors.forename: Y S
authors.initials: YS
authors.lastname: Or
authors.forename: D T
authors.initials: DT
authors.lastname: Chu
authors.forename: Z
authors.initials: Z
authors.lastname: Ma
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D004917:Erythromycin / Q000031:analogs & derivatives*
chemical_list: D000900:Anti-Bacterial Agents; D004917:Erythromycin