Abstract
A stereoselective method is described for the synthesis of [3.3.0] fused lactones (γ-butyrolactones) of carbohydrates at the 2 and 3 positions of the furanose ring, by intramolecular addition of radicals onto the α-position of α,β-unsaturated esters. A new stereogenic center is formed at an off-template site of the ribofuranose ring, with good diastereoselectivity. Stereocontrol is discussed on the basis of conformational preference in the transition state. These γ-butyrolactones of carbohydrates are useful chiral synthons for the preparation of branched-chain sugars. Opening of the lactone ring afforded homochiral branched-chain sugars having a highly functionalized C-branch at C-2 or C-3.
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