Palladium-catalyzed synthesis of uridines on polystyrene-based solid supports.
In this paper, the solid-phase synthesis of various substituted pyrimidine nucleosides is described starting from 2'-deoxyuridine, which has been attached through a base labile linker to polystyrene resins. The utility of the Pd(0) cross-coupling to functionalized pyrimidine nucleosides is expanded herein to include reactions of resin-supported 5-iodo-2'-deoxyuridine under Sonogashira, Stille, Heck, and Suzuki conditions. Upon cleavage with MeONa, a library of 5-substituted pyrimidine nucleosides was obtained in good (under Sonogashira and Stille conditions) to moderate (under Heck or Suzuki conditions) yields and high purity. Except the Suzuki-type reactions, the presented methods exhibit a significant improvement and facilitate the synthetic procedure with respect to purification and yields (determined after filtration over silica gel).
Aucagne
Vincent
V
Institut de Chimie Organique et Analytique, UMR CNRS 6005, Université d'Orléans BP 6759, 45067 Orléans Cedex 2, France.
Berteina-Raboin
Sabine
S
Guenot
Pierre
P
Agrofoglio
Luigi A
LA
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D010165:Palladium / Q000737:chemistry; D011137:Polystyrenes; D011742:Pyrimidine Nucleotides / Q000737:chemistry; D012117:Resins, Synthetic; D014500:Uracil Nucleotides / Q000138:chemical synthesis*
D011137:Polystyrenes; D011742:Pyrimidine Nucleotides; D012117:Resins, Synthetic; D014500:Uracil Nucleotides; D010165:Palladium