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Synlett 1992; 1992(1): 67-69
DOI: 10.1055/s-1992-21269
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The Stereoselective Photochemical Addition of Alcohols to 5-Substituted Furan-2(5H)-ones

John Mann* , Alexander Weymouth-Wilson
  • *Department of Chemistry, Reading University, Whiteknights, P.O. Box 224, Reading, RG6 2AD, England
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Publication Date:
18 September 2002 (online)

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We describe a practical route to anti-5-substituted 4-hydroxyalkyltetrahydrofuran-2-ones via the stereoselective photochemically mediated addition of alcohols to (5R)- and (5S)-5-substituted furan-2(5H)-ones. These products have been converted into stereochemically defined 4-substituted 3-oxabicyclo[3.1.0]hexan-2-ones, which are potential intermediates for the synthesis of chrysanthemic acids and other cyclopropyl compounds. In addition, the adducts can be converted into 3-substituted 2,3-dideoxynucleosides.