title: Total synthesis of (-)-4,8,10-tridesmethyl telithromycin.
abstract: Novel sources of antibiotics are required to address the serious problem of antibiotic resistance. Telithromycin (2) is a third-generation macrolide antibiotic prepared from erythromycin (1) and used clinically since 2004. Herein we report the details of our efforts that ultimately led to the total synthesis of (-)-4,8,10-tridesmethyl telithromycin (3) wherein methyl groups have been replaced with hydrogens. The synthesis of desmethyl macrolides has emerged as a novel strategy for preparing bioactive antibiotics.
authors.affiliation: Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA.
authors.forename: Venkata
authors.initials: V
authors.lastname: Velvadapu
authors.forename: Tapas
authors.initials: T
authors.lastname: Paul
authors.forename: Bharat
authors.initials: B
authors.lastname: Wagh
authors.forename: Ian
authors.initials: I
authors.lastname: Glassford
authors.forename: Charles
authors.initials: C
authors.lastname: DeBrosse
authors.forename: Rodrigo B
authors.initials: RB
authors.lastname: Andrade
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D048628:Ketolides / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy
chemical_list: D000900:Anti-Bacterial Agents; D048628:Ketolides; C106791:telithromycin