Palladium-catalyzed cross-coupling reactions in c6 modifications of purine nucleosides.
This unit describes the cross-coupling methodology for introduction of diverse C-substituents to position 6 of purine nucleosides. Protected 6-chloropurine nucleosides undergo Pd-catalyzed cross-coupling reactions with trialkylaluminium, alkylzinc halides, aryl(tributyl)stannanes, and arylboronic acids to give the corresponding 6-substituted intermediates, which can be deprotected by treatment with NaOMe. (Acetyloxy)methylzinc iodide is used for introduction of the hydroxymethyl group, which can further be transformed to fluoromethyl and difluoromethyl groups. Most of the title 6-substituted purine ribonucleosides possess cytostatic and/or anti-HCV activity.
Hocek
Michal
M
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague, Czech Republic.
Silhár
Peter
P
D002384:Catalysis; D009682:Magnetic Resonance Spectroscopy; D010165:Palladium / Q000737:chemistry*; D011684:Purine Nucleosides / Q000737:chemistry*
D011684:Purine Nucleosides; D010165:Palladium