title: Total synthesis of 3',5'-C-branched nucleosides.
abstract: [reaction: see text] A novel total synthesis of 3',5'-C-branched uridine azido acid has been accomplished using stereoselective aldehyde alkynylation, Ireland-Claisen rearrangement, and iodolactonization as the key reactions. Compared to traditional routes that start from carbohydrates, the present methodology is more efficient, flexible for future optimization, and provides access to both enantiomers of the products. Because the key chemistry does not involve the 3'- and 5'-C substituents, our route is a general approach to 3',5'-C alkyl nucleoside analogues.
authors.affiliation: Department of Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts 02115, USA. e.rozners@neu.edu
authors.forename: Eriks
authors.initials: E
authors.lastname: Rozners
authors.forename: Qun
authors.initials: Q
authors.lastname: Xu
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D003500:Cyclization; D009705:Nucleosides / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014529:Uridine / Q000031:analogs & derivatives / Q000138:chemical synthesis
chemical_list: D000480:Alkynes; D001386:Azides; D009705:Nucleosides; D014529:Uridine