Synthesis of pyrrolidine C-nucleosides via Heck reaction.
[figure: see text] A novel method for the synthesis of pyrrolidine C-nucleosides has been developed. The key step of the synthesis is the palladium(0)-mediated coupling of a disubstituted N-protected 2-pyrroline and 5-iodouracil. C-Nucleoside 14 and its N-methyl derivative 15 can easily be converted to the corresponding phosphoramidite building blocks for DNA synthesis.
Häberli
A
A
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland.
Leumann
C J
CJ
D009705:Nucleosides / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis*
D009705:Nucleosides; D011759:Pyrrolidines; D010165:Palladium