Synthesis of mono- and bis-C-glycosylated 2,3,4-trisubstituted 1H-pyrroles as cyclo- and acyclo-C-nucleoside analogues

5 pages, 1 table, 3 schemes.
A new method for the synthesis of mono- and bis-C-glycosylated 2,3,4-trisubstituted 1H-pyrroles, a type of cyclo- and ­acyclo-C-nucleoside analogues, is described. The reaction of readily available sensitive 2H-azirines derived from carbohydrates with 1,3-dicarbonyl compounds is catalysed by tris(triphenylsilyl)vanadate under mild conditions. The reaction of 2H-azirines with vanadium enolates has not been described previously. This methodology may be suitable for the synthesis of combinatorial libraries with the trisubstituted 1H-pyrrole skeleton as a molecular scaffold.
This work was supported by the Investigation programs No. CTQ2004-06381/BQU and CTQ2004-02367/BQU of the Ministerio de Educación y Ciencia, Spain, cofinanced with the Fondo Europeo de Desarrollo Regional (FEDER). C.R.A. thanks the I3P-CSIC program for a fellowship.