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Synlett 1994; 1994(2): 115-116
DOI: 10.1055/s-1994-22759
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Observations on the Modified Fujimoto-Belleau Approach to Mannose-Derived Carbocyclic Sugars

Mahmoud Aloui* , Barry Lygo, H. Trabsa
  • *Department of Chemistry and Applied Chemistry, University of Salford, Salford M5 4WT, UK.
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Publication Date:
22 March 2002 (online)

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It has been found that the Wadsworth-Emmons modification of the Fujimoto-Belleau approach to carbocycles from carbohydrates can selectively give vinyl phosphonate rather than the expected enone, depending upon the carbohydrate stereochemistry. Utility of the vinyl phosphonate product in the synthesis of a novel D-myo-inositol-4-phosphate analogue is reported, and a method for the conversion of the vinylphosphonate to the corresponding enone has been developed.

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