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Synthesis 2010(24): 4199-4206  
DOI: 10.1055/s-0030-1258318
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Phenol and Pyridone C-Ribo- and 2′-Deoxyribonucleosides by Palladium-Catalyzed Hydroxylations of Haloaryl C-Nucleosides

Martin Štefko, Michal Hocek*
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead & IOCB Research Center, Flemingovo nam. 2, 16610, Prague 6, Czech Republic
Fax: +420 220183559; e-Mail: hocek@uochb.cas.cz;
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Publication History

Received 25 August 2010
Publication Date:
28 October 2010 (online)

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Abstract

Phenol and pyridone C-nucleosides in both ribo- and deoxyribo series were prepared by palladium-catalyzed hydroxylations reactions from the corresponding TBS-protected bromophenyl and bromo- or chloropyridyl C-nucleosides using Buchwald-type ligand under mild conditions. Partial or complete desilylation of 5′-OH was observed in some cases. Free nucleosides (7 examples) were obtained in good overall yields by cleavage of TBS-protecting groups with Et3N˙3HF.

Key words

C-nucleoside - palladium-catalyzed - hydroxylations - phenol - pyridone

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