title: Total synthesis of pikromycin.
abstract: The total synthesis of pikromycin (6), the first isolated macrolide antibiotic, was achieved. The target macrolide was retrosynthetically divided into two parts, pikronolide (6a) (aglycon) and D-desosamine. The aglycon was synthesized using key reactions such as an asymmetric aldol reaction, Yamaguchi esterification, and ring-closing metathesis. The aglycon was coupled successfully with the trichloroacetimidate derivative of D-desosamine under Lewis acidic conditions to afford pikromycin. Narbomycin (5) was also synthesized from narbonolide (5a) under identical conditions.
authors.affiliation: Department of Chemistry, Chungbuk National University, Cheongju, Chungbuk 361-763, Korea.
authors.forename: Hong-Se
authors.initials: HS
authors.lastname: Oh
authors.forename: Han-Young
authors.initials: HY
authors.lastname: Kang
mesh_terms: D000606:Amino Sugars / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000606:Amino Sugars; D000900:Anti-Bacterial Agents; D018942:Macrolides; C517337:narbonolide; C010488:narbomycin; C110125:desosamine; C003145:picromycin