title: Synthesis of 7-oxabicyclo[2.2.1]heptanes and 8-oxabicyclo[3.2.1]octanes from C-glycosides via an intramolecular cyclization.
abstract: A simple and effective method for the synthesis of 7-oxabicyclo[2.2.1]heptanes and 8-oxabicyclo[3.2.1]octanes from acetonyl C-glycoside substrates is described, which involves an intramolecular cyclization reaction through a nucleophilic substitution at C-5 or C-6 of C-glycosides by a 2'-enamine intermediate formed in the presence of pyrrolidine. Because anomeric epimerization occurs under these conditions, C-glycoside substrates with either anomeric configuration were converted to the same product(s) in same stereoselectivity and similar chemical yield.
authors: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario K1A 0R6, Canada. wei.zou@nrc-cnrc.gc.ca
authors: Wei
authors: W
authors: Zou
authors: Kannan
authors: K
authors: Vembaiyan
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D003508:Cycloheptanes / Q000138:chemical synthesis* / Q000737:chemistry; D034242:Cyclooctanes / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001643:Bridged Bicyclo Compounds; C438934:C-glycoside; D003508:Cycloheptanes; D034242:Cyclooctanes; D006027:Glycosides; D009005:Monosaccharides