title: Convergent de novo synthesis of vineomycinone B2 methyl ester.
abstract: An efficient de novo synthesis of vineomycinone B2 methyl ester has been achieved. The longest linear route required only 14 steps from achiral commercially available starting materials (4.0% overall yield). The key transformations included the de novo asymmetric synthesis of two key fragments, which were joined by a convergent late stage Suzuki's glycosylation for the construction of the aryl β-C-glycoside. A subsequent BBr3 one-pot debenzylation, demethylation and air oxidation provided vineomycinone B2 methyl ester.
authors.affiliation: Guangdong University of Technology, Guangzhou 510006, China.
authors.forename: Qian
authors.initials: Q
authors.lastname: Chen
authors.forename: Yashan
authors.initials: Y
authors.lastname: Zhong
authors.forename: George A
authors.initials: GA
authors.lastname: O'Doherty
mesh_terms: D000880:Anthraquinones / Q000138:chemical synthesis*; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D004952:Esters / Q000138:chemical synthesis; D005643:Fucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006027:Glycosides; D008745:Methylation; D009005:Monosaccharides / Q000737:chemistry; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D000880:Anthraquinones; D000903:Antibiotics, Antineoplastic; C438934:C-glycoside; D004952:Esters; D006027:Glycosides; D009005:Monosaccharides; C585971:vineomycinone B2 methyl ester; D005643:Fucose