Toward amide-linked RNA mimics: total synthesis of 3'-C branched uridine azido acid via an ene-iodolactonization approach.
[reaction: see text] A novel synthesis of 3'-C branched uridine azido acid has been accomplished by a sequence of stereoselective ene and iodolactonization reactions. Compared to traditional routes that start from carbohydrates, the present methodology is more flexible and can be further optimized by incorporation of novel future developments of synthetic chemistry. Because the key chemistry does not involve the 3'-C substituent, our route is a general approach to 3'-C alkyl nucleoside analogues.
Rozners
Eriks
E
Department of Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts 02115, USA. e.rozners@neu.edu
Liu
Yang
Y
D001386:Azides; D018716:Molecular Mimicry; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis*; D012313:RNA / Q000737:chemistry; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D001386:Azides; D020135:Peptide Nucleic Acids; D012313:RNA; D014529:Uridine