A General Route to 4-C-Substituted Pyrimidine Nucleosides

Ulrich Hennecke; David Kuch; Thomas Carell

doi:10.1055/s-2007-965935

PAPER

A General Route to 4-C-Substituted Pyrimidine Nucleosides

Ulrich Hennecke, David Kuch, Thomas Carell*
Fakultät für Chemie und Pharmazie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13 Haus F, 81377 München, Germany
Fax: +49(89)218077756; e-Mail: thomas.carell@cup.uni-muenchen.de;

Abstract

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Abstract

Palladium-catalyzed cross-coupling reactions of tin and zinc nucleophiles with arylsulfonates of pyrimidine nucleosides have been achieved to give a wide range of 4-C-substituted pyrimidine nucleosides. This method also allows the construction of pyrimidine-pyrimidinone dinucleosides, containing the carbon skeleton of the (6-4) DNA photo lesion.

Key words

cross-coupling - nucleosides - palladium - pyrimidines - (6-4) lesion

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