Carbohydrate Research 2006-07-24

De novo asymmetric syntheses of C-4-substituted sugars via an iterative dihydroxylation strategy.

Md Moinuddin Ahmed, George A O'Doherty

Index: Carbohydr. Res. 341(10) , 1505-21, (2006)

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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.