title: Synthesis of (E)-3'-phosphonoalkenyl modified nucleoside phosphonates via a highly stereoselective olefin cross-metathesis reaction.
abstract: The synthesis of (E)-3'-phosphonoalkenyl and 3'-phosphonoalkyl modified nucleoside analogues with a β-D-erythrofuranose moiety is reported. The highly stereoselective olefin cross-metathesis reaction was applied to introduce the phosphonoalkenyl group at the 3'-position of the sugar moiety with absolute (E)-selectivity. The 3',6'-cyclomonophosphonic acids of 3'-phosphonoethyl-β-D-erythrofuranosyl nucleosides were synthesized via a dehydrative intramolecular cyclization reaction. None of the synthesized compounds shows significant in vitro activity against HIV, HCV, and RSV.
authors.affiliation: Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, K.U. Leuven, Leuven B-3000, Belgium.
authors.forename: Qiuya
authors.initials: Q
authors.lastname: Huang
authors.forename: Piet
authors.initials: P
authors.lastname: Herdewijn
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D003500:Cyclization; D009705:Nucleosides / Q000737:chemistry*; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism; D013379:Substrate Specificity; D014780:Viruses / Q000187:drug effects
chemical_list: D000475:Alkenes; D000998:Antiviral Agents; D009705:Nucleosides; D063065:Organophosphonates