Highly functionalized and potent antiviral cyclopentane derivatives formed by a tandem process consisting of organometallic, transition-metal-catalyzed, and radical reaction steps

Pratap R. Jagtap, Leigh Ford, Elmar Deister, Radek Pohl, Ivana Císařová, Jan Hodek, Jan Weber, Richard Mackman, Gina Bahador, Ullrich Jahn

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11 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)10298-10304
Number of pages7
JournalChemistry - A European Journal
Volume20
Issue number33
DOIs
Publication statusPublished - 11 Aug 2014

Keywords

  • antiviral activity
  • cyclopentanes
  • isomerization
  • organic synthesis
  • radicals

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