Synthesis of C-furanosides from a D-glucal-derived cyclopropane through a ring-expansion/ring-contraction sequence.
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.
Hewitt
Russell J
RJ
School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington, New Zealand.
Harvey
Joanne E
JE
D003521:Cyclopropanes / Q000737:chemistry*; D003847:Deoxyglucose / Q000031:analogs & derivatives* / Q000737:chemistry; D005630:Fructans / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation
D003521:Cyclopropanes; D005630:Fructans; C001289:d-glucal; C030797:cyclopropane; D003847:Deoxyglucose