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  • Title: De novo asymmetric syntheses of C-4-substituted sugars via an iterative dihydroxylation strategy.
    Author: Ahmed MM, O'Doherty GA.
    Journal: Carbohydr Res; 2006 Jul 24; 341(10):1505-21. PubMed ID: 16616898.
    Abstract:
    A short and highly efficient route to various C-4 substituted sugar lactones has been developed. The key to the overall transformation is the sequential osmium-catalyzed dihydroxylation reaction of substituted 2,4-dienoates and an allylic substitution at the C-4 position. When the Sharpless AD-mix procedure is used in a matched sense for the second dihydroxylation reaction, it results in an exceedingly diastereo- and enantioselective synthesis of several C-4-substituted sugars.
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