title: Synthesis of the branched C-glycoside substructure of altromycin B.
abstract: Tungsten-catalyzed cycloisomerization of alkynyl alcohols including 8 provides only the endocyclic enol ether (11) as a key intermediate for the branched C-glycoside substructure (2) of altromycin B. A sequence of Stille cross-coupling reaction and regio- and stereoselective functional group transformations affords each C13-diastereomer of the branched C-arylglycoside (2a and 2b). [reaction: see text]
authors.affiliation: Department of Chemistry, Emory University, Atlanta, GA 30322, USA.
authors.forename: Bonsuk
authors.initials: B
authors.lastname: Koo
authors.forename: Frank E
authors.initials: FE
authors.lastname: McDonald
mesh_terms: D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism; D014414:Tungsten / Q000737:chemistry
chemical_list: D000617:Aminoglycosides; C063717:altromycin B; D014414:Tungsten