title: Studies toward the total synthesis of pluraflavin A.
abstract: A synthetic strategy towards the potent cytostatic agent pluraflavin A has been developed. Formation of the enantioenriched anthrapyran core bearing a halogen atom enabled the introduction of the α C-aryl glycoside by Stille cross-coupling and subsequent hydrogenation of the aryl glycal. Chemo- and stereoselective O-glycosylations of α oliose and β 3-epi vancosamine residues afforded a fully glycosylated aromatic core. Attempts to install the dimethylamino group of the C-disaccharide suggest that introduction of an azide group by displacement and subsequent reduction may pave the way to the total synthesis of pluraflavin A.
authors.affiliation: Department of Chemistry, Columbia University, 3000 Broadway, New York, NY 10027 (USA).
authors.forename: John
authors.initials: J
authors.lastname: Hartung
authors.forename: Benjamin
authors.initials: B
authors.lastname: J D Wright
authors.forename: Samuel J
authors.initials: SJ
authors.lastname: Danishefsky
mesh_terms: D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D013237:Stereoisomerism
chemical_list: D000880:Anthraquinones; D001688:Biological Products; C440630:pluraflavin A
keywords: C-glycoside; anti-cancer agents; glycosylation; pluraflavin A; pluramycins