title: Synthesis of C-furanosides from a D-glucal-derived cyclopropane through a ring-expansion/ring-contraction sequence.
abstract: gem-Dibromocyclopropane 1, prepared from tri-O-benzyl-D-glucal, undergoes thermal and silver-promoted ring expansion in the presence of alcohols to give substituted oxepines. With further heating, ring contraction to highly substituted tetrahydrofurans follows. These represent C-furanosides, potentially useful as precursors to C-nucleosides and other carbohydrate mimics.
authors.affiliation: School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington, New Zealand.
authors.forename: Russell J
authors.initials: RJ
authors.lastname: Hewitt
authors.forename: Joanne E
authors.initials: JE
authors.lastname: Harvey
mesh_terms: D003521:Cyclopropanes / Q000737:chemistry*; D003847:Deoxyglucose / Q000031:analogs & derivatives* / Q000737:chemistry; D005630:Fructans / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation
chemical_list: D003521:Cyclopropanes; D005630:Fructans; C001289:d-glucal; C030797:cyclopropane; D003847:Deoxyglucose