Abstract
A new method for the synthesis of mono- and bis-C-glycosylated 2,3,4-trisubstituted 1 H-pyrroles, a type of cyclo- and -acyclo- C-nucleoside analogues, is described. The reaction of readily available sensitive 2 H-azirines derived from carbohydrates with 1,3-dicarbonyl compounds is catalysed by tris(triphenylsilyl)vanadate under mild conditions. The reaction of 2 H-azirines with vanadium enolates has not been described previously. This methodology may be suitable for the synthesis of combinatorial libraries with the trisubstituted 1 H-pyrrole skeleton as a molecular scaffold.
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