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Issue 1, 2011
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Synthesis of C-furanosides from a D-glucal-derived cyclopropane through a ring-expansion/ring-contraction sequence

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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.

Graphical abstract: Synthesis of C-furanosides from a d-glucal-derived cyclopropane through a ring-expansion/ring-contraction sequence

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The article was received on 30 Jun 2010, accepted on 31 Aug 2010 and first published on 20 Sep 2010


Article type: Communication
DOI: 10.1039/C0CC02244F
Chem. Commun., 2011,47, 421-423

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    Synthesis of C-furanosides from a D-glucal-derived cyclopropane through a ring-expansion/ring-contraction sequence

    R. J. Hewitt and J. E. Harvey, Chem. Commun., 2011, 47, 421
    DOI: 10.1039/C0CC02244F

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