title: Hybrid aminoglycoside antibiotics via Tsuji palladium-catalyzed allylic deoxygenation.
abstract: Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an α,β-unsaturated 6'-aldehyde and an allylic 3'-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol % Pd(2)(dba)(3) and Bu(3)P granted access to a novel series of 3',4'-dideoxy-4',5'-dehydro ring A hybrids. The neomycin-sisomicin hybrid exhibited superior in vitro antibacterial activity to the parent compound neomycin.
authors.affiliation: Department of Chemistry, Université de Montréal, C. P. 6128, Succ. Centre-Ville, Montréal, QC, Canada, H3C 3J7. stephen.hanessian@umontreal.ca
authors.forename: Stephen
authors.initials: S
authors.lastname: Hanessian
authors.forename: Juan Pablo
authors.initials: JP
authors.lastname: Maianti
authors.forename: Rowena D
authors.initials: RD
authors.lastname: Matias
authors.forename: Lee Ann
authors.initials: LA
authors.lastname: Feeney
authors.forename: Eliana S
authors.initials: ES
authors.lastname: Armstrong
mesh_terms: D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D009355:Neomycin / Q000737:chemistry; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D010303:Paromomycin / Q000737:chemistry; D012853:Sisomicin / Q000737:chemistry
chemical_list: D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D010165:Palladium; D010303:Paromomycin; D009355:Neomycin; D012853:Sisomicin