title: Synthesis of 3',3'-difluoro-2'- hydroxymethyl-4',5'-unsaturated carbocyclic nucleosides.
abstract: 3',3'-Difluoro-2'-hydroxymethyl-4',5'-unsaturated carbocyclic nucleosides 1-3 have been stereoselectively synthesized from ester 10, which can be conveniently prepared from 2,3-isopropylidene-d-glyceraldehyde 7 in five steps. The whole synthesis highlighted the stereoselective Reformatskii-Claisen rearrangement, ring-closing metathesis (RCM), and palladium-catalyzed allylic alkylation, in which the regioselectivity was reversed from that of nonfluorinated substrates.
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
authors.forename: Yan-Yan
authors.initials: YY
authors.lastname: Yang
authors.forename: Jun
authors.initials: J
authors.lastname: Xu
authors.forename: Zheng-Wei
authors.initials: ZW
authors.lastname: You
authors.forename: Xiu-Hua
authors.initials: XH
authors.lastname: Xu
authors.forename: Xiao-Long
authors.initials: XL
authors.lastname: Qiu
authors.forename: Feng-Ling
authors.initials: FL
authors.lastname: Qing
mesh_terms: D000478:Alkylation; D003500:Cyclization; D009705:Nucleosides / Q000138:chemical synthesis*
chemical_list: D009705:Nucleosides