title: A streamlined strategy for aglycone assembly and glycosylation.
abstract: Multipurpose sugars: Carbohydrate-derived silane reagents are utilized as the reductant for nickel-catalyzed aldehyde-alkyne reductive coupling reactions and as the glycosyl donor for subsequent intramolecular glycosylation. The approach enables the assembly of the carbon-carbon framework and stereochemical features of an aglycone while simultaneously establishing the site of glycosylation.
authors.affiliation: Department of Chemistry, University of Michigan, Ann Arbor, MI 48109-1055 (USA) http://www.umich.edu/∼jmgroup.
authors.forename: Katherine M
authors.initials: KM
authors.lastname: Partridge
authors.forename: Scott J
authors.initials: SJ
authors.lastname: Bader
authors.forename: Zachary A
authors.initials: ZA
authors.lastname: Buchan
authors.forename: Christopher E
authors.initials: CE
authors.lastname: Taylor
authors.forename: John
authors.initials: J
authors.lastname: Montgomery
mesh_terms: D002384:Catalysis; D006031:Glycosylation; D009532:Nickel / Q000737:chemistry*; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009532:Nickel; D012825:Silicon
keywords: glycosylation; multicomponent reactions; nickel; silicon; synthetic methods