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Synlett 1997; 1997(2): 211-213
DOI: 10.1055/s-1997-736
DOI: 10.1055/s-1997-736
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Stereospecific Synthesis of Spirohydantoins of β-Glucopyranose: Inhibitors of Glycogen Phosphorylase
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Publication History
Publication Date:
31 December 2000 (online)
A stereospecific synthesis of the spirohydantoin of glucopyranose 1β [a potent and specific inhibitor of glycogen phosphorylase (GP)] and of a number of spirohydantoin analogues thereof relies on the rigidity of a bicyclic lactone 2. The effects of these analogues on GP are reported.
The epimeric azides 1 may be transformed into the bicyclic intermediate 2 which is a divergent precursor for the stereospecific synthesis of β-spirohydantoins of glucopyranose 3 which were evaluated as inhibitors of glycogen phosphorylase.