title: Synthesis of the pluramycins 1: two designed anthrones as enabling platforms for flexible bis-C-glycosylation.
abstract: Two effective tricyclic platforms are reported for the installation of the two constituent sugars, L-vancosamine and D-angolosamine, in a regio- and stereoselective manner for the synthesis of the pluramycin class of bis-C-glycoside antitumor antibiotics. Two complementary protocols are now available that differ in the order in which the two sugar moieties are installed. Sc(OTf)3 was effective as the Lewis acid.
authors.affiliation: Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551 (Japan) http://www.chemistry.titech.ac.jp/∼org_synth/
authors.forename: Kei
authors.initials: K
authors.lastname: Kitamura
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Ando
authors.forename: Takashi
authors.initials: T
authors.lastname: Matsumoto
authors.forename: Keisuke
authors.initials: K
authors.lastname: Suzuki
mesh_terms: D000606:Amino Sugars / Q000737:chemistry; D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D000873:Anthracenes / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides; D006031:Glycosylation; D006595:Hexosamines / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry; D009005:Monosaccharides / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000606:Amino Sugars; D000617:Aminoglycosides; D000873:Anthracenes; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; C438934:C-glycoside; D006027:Glycosides; D006595:Hexosamines; D058116:Lewis Acids; D009005:Monosaccharides; C003169:pluramycin; C001946:vancosamine
keywords: C-glycosylation; Lewis acids; amino sugars; bis-C-glycosides; pluramycins