An
efficient, divergent, and straightforward access to novel C-glycosides has been developed, namely, α-hydroxy
carboxamide and carboxylic acid derivatives, via a green and scalable
process from unprotected carbohydrates. The method involves condensation
of 1,3-dimethylbarbituric acid with unprotected sugars followed by
subsequent barbiturate oxidative cleavage in the same pot. Further
expanding of the chemistry led to the development of efficient entries
to diastereoisomerically pure C-glycosyl-α-hydroxy
esters or amides through nucleophilic attack on a readily available
and versatile key lactone intermediate.
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