title: Highly functionalized and potent antiviral cyclopentane derivatives formed by a tandem process consisting of organometallic, transition-metal-catalyzed, and radical reaction steps.
abstract: A simple modular tandem approach to multiply substituted cyclopentane derivatives is reported, which succeeds by joining organometallic addition, conjugate addition, radical cyclization, and oxygenation steps. The key steps enabling this tandem process are the thus far rarely used isomerization of allylic alkoxides to enolates and single-electron transfer to merge the organometallic step with the radical and oxygenation chemistry. This controlled lineup of multiple electronically contrasting reactive intermediates provides versatile access to highly functionalized cyclopentane derivatives from very simple and readily available commodity precursors. The antiviral activity of the synthesized compounds was screened and a number of compounds showed potent activity against hepatitis C and dengue viruses.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo namesti 2, 16610 Prague (Czech Republic).
authors.forename: Pratap R
authors.initials: PR
authors.lastname: Jagtap
authors.forename: Leigh
authors.initials: L
authors.lastname: Ford
authors.forename: Elmar
authors.initials: E
authors.lastname: Deister
authors.forename: Radek
authors.initials: R
authors.lastname: Pohl
authors.forename: Ivana
authors.initials: I
authors.lastname: Císařová
authors.forename: Jan
authors.initials: J
authors.lastname: Hodek
authors.forename: Jan
authors.initials: J
authors.lastname: Weber
authors.forename: Richard
authors.initials: R
authors.lastname: Mackman
authors.forename: Gina
authors.initials: G
authors.lastname: Bahador
authors.forename: Ullrich
authors.initials: U
authors.lastname: Jahn
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D003715:Dengue / Q000188:drug therapy; D003716:Dengue Virus / Q000187:drug effects; D016174:Hepacivirus / Q000187:drug effects; D006526:Hepatitis C / Q000188:drug therapy; D006801:Humans; D007536:Isomerism; D008958:Models, Molecular; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D028561:Transition Elements / Q000737:chemistry
chemical_list: D000998:Antiviral Agents; D003517:Cyclopentanes; D009942:Organometallic Compounds; D028561:Transition Elements
keywords: antiviral activity; cyclopentanes; isomerization; organic synthesis; radicals