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Title

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

AuthorsAlonso-Cruz, Carmen R. ; Freire, Raimundo ; Rodríguez Morales, María S. ; Suárez, Ernesto
KeywordsPyrroles
Heterocycles
Addition reactions
C-nucleosides
C-glycosides
Issue Date25-Sep-2007
PublisherThieme
CitationSynlett 17: 2723-2727 (2007)
AbstractA 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.
Description5 pages, 1 table, 3 schemes.
Publisher version (URL)http://dx.doi.org/10.1055/s-2007-991061
URIhttp://hdl.handle.net/10261/12682
DOI10.1055/s-2007-991061
ISSN0936-5214
Appears in Collections:(IPNA) Artículos
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