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Synthesis 1995; 1995(5): 544-552
DOI: 10.1055/s-1995-3945
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Synthesis of New Cyclopropano Furanosides: Construction of a 2-Oxabicyclo[3.1.0]hexane Skeleton by a One-Pot 1,2-Diol Monosulfonate Rearrangement-Cyclopropanation Reaction

Masajiro Kawana* , Hiroyoshi Kuzuhara
  • *The Institute of Physical and Chemical Research (RIKEN), Wako, Saitama 351-01, Japan, Fax +81(484)621111
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Publication Date:
31 December 2000 (online)

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The synthesis and characterization of new methyl cyclopropano furanosides are described. A fused cyclopropane ring bearing a hydroxymethyl group was constructed at the 3,4-positions of the furanose ring by a consecutive 1,2-hydride shift-enolization-cyclopropanation reaction starting from a sugar disulfonate under mild reaction conditions with Mg(OMe)2 in a one-pot manner.

1,2-diol monosulfonate rearrangement - 1,2-hydride shift - cyclopropanation - cyclopropano sugar - 2-oxabicyclo[3.1.0]hexane derivative