Development of a general and modular approach to C-nucleosides

0361522 - ÚOCHB 2012 CZ eng C - Konferenční příspěvek (zahraniční konf.)
Kubelka, Tomáš - Štefko, Martin - Bárta, Jan - Joubert, Nicolas - Urban, Milan - Chapuis, Hubert Jean - Hocek, Michal
Development of a general and modular approach to C-nucleosides.
Chemistry of Nucleic Acid Components. 15th Symposium. Praha: Institute of Organic Chemistry and Biochemistry AS CR, v. v. i., 2011 - (Hocek, M.), s. 180-183. Collection Symposium Series, 12. ISBN 978-80-86241-37-1.
[Chemistry of Nucleic Acid Components /15./. Český Krumlov (CZ), 05.06.2011-10.06.2011]
Grant CEP: GA MŠMT LC512; GA AV ČR IAA400550902
Výzkumný záměr: CEZ:AV0Z40550506
Klíčová slova: C-nucleosides * cross-coupling * palladium
Kód oboru RIV: CC - Organická chemie

Highly efficient and modular approach was developed for the synthesis of various types of new (het)aryl C-nucleosides. This protocol consists of the synthesis of haloaryl-C-nucleoside intermediates, followed by a functional group transformation to introduce various substituents. Using this approach protected 2′-deoxy-C-nucleosides bearing halogenated benzene, pyridine, thiophene, furane and pyrimidine were prepared. These intermediates were then submitted to a wide range of palladium-catalyzed reactions. The same approach was also used for preparation of C-nucleosides bearing ribofuranose moiety. Functional ribofuranosides bearing diverse substituted pyridine and benzene nucleobases were prepared in this way.
Trvalý link: http://hdl.handle.net/11104/0198820