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Synlett 1996; 1996(12): 1218-1220
DOI: 10.1055/s-1996-5709
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A Novel Approach to Furanoid Sugars via 1,4-Iodocyclization of Pyranoid D-Galactal

Véronique Jaouen, Anne Jégou, Alain Veyrières*
  • *Laboratoire de Synthèses et Activations de Biomolécules, CNRS URA 1467, Ecole Nationale Supérieure de Chimie de Rennes, Campus de Beaulieu, 35700 Rennes, France, Fax +33(2)99871348
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Publication Date:
31 December 2000 (online)

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Iodocyclization of 6-O-pivaloyl-D-galactal, followed by radical reduction, gives a rigid [2.2.1] bicyclic acetal which is regioselectively opened by various nucleophiles (alcohols, triphenylphosphine, allyltrimethylsilane) under mild acidic conditions to give furano compounds in good yields.

[2.2.1]bicyclic acetals - furanosides - D-galactal - iodocyclization - Wittig reaction

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