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1 Polish Journal of Chemistry

1 2000

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C(2)-(alfa-Mannosyl)indole: The Pivotal Intermediate Towards the Natural C-Glycopeptides

100%

Hassan H. H. A. M. , Spies H. S. , Bredenkamp M. W.

tom Vol. 74, nr 11

15889-1598

Two different approaches were investigated to prepare the unusual modified peptide C(2)-mannosylated indole residue. Direct glycosylation of 2-metallated indoles or 2-trimethylsilylindole derivative by reaction with perbenzylated -D-mannopyranosyl bromide was incompatible due to the intermediate generation of a nucleophilic anomeric carbon atom followed by elimination of the functional group at C-2. Palladium-catalyzed coupling/cyclization approach was examined as a novel route towards indole-(C)- glycosides. Coupling of the mannopyranosyl donors with o-ethynylaniline derivative in the presence of Pd(0) followed by cyclization of the newly formed alditols were also described.