title: Novel synthesis of 4'C-aryl-branched acyclic nucleoside using [3,3]-sigmatropic rearrangement.
abstract: A very efficient synthetic route for preparing a novel 4'-C-aryl branched-1',2'-seco-2',3'-dideoxy-2',3'-didehydro-nucleoside is described. Mesylate 7 was successfully synthesized via a Horner-Wadsworth-Emmons reaction and a [3,3]-sigmatropic rearrangement, with which an adenine base was coupled by nucleophilic substitution conditions (K2CO3, 18-Crown-6, DMF) to give the target nucleoside 9.
authors.affiliation: Department of Chemistry, Korea University, Anam-dong, Sungbuk-ku, Seoul, South Korea.
authors.forename: Gun Ha
authors.initials: GH
authors.lastname: Baik
authors.forename: Bong Young
authors.initials: BY
authors.lastname: Chung
authors.forename: Chang-Hyun
authors.initials: CH
authors.lastname: Oh
authors.forename: Jung-Hyuck
authors.initials: JH
authors.lastname: Cho
authors.forename: Ok Hyun
authors.initials: OH
authors.lastname: Ko
authors.forename: Joon Hee
authors.initials: JH
authors.lastname: Hong
mesh_terms: D000225:Adenine / Q000737:chemistry; D019380:Anti-HIV Agents / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis*
chemical_list: D019380:Anti-HIV Agents; D009705:Nucleosides; D000225:Adenine