The Shortest Strategy for Generating Phosphonate Prodrugs by Olefin Cross-Metathesis - Application to Acyclonucleoside Phosphonates

Ugo Pradere, Herve Clavier, Vincent Roy, Steven P. Nolan, Luigi A. Agrofoglio

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

A short synthetic route to phosphonate prodrugs by olefin cross-metathesis, which uses either (acyloxymethyl) or (hexadecyloxypropyl) allylphosphonate building blocks is described. A study of eight ruthenium catalysts including the Ruindenylidene catalyst, which bears the N-heterocyclic carbene 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene, was undertaken. This method was applied to the synthesis of acyclonucleoside phosphonate prodrugs. This strategy is appealing for further uses in pharmaceutical and medicinal research.

Original languageEnglish
Pages (from-to)7324-7330
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number36
DOIs
Publication statusPublished - Dec 2011

Keywords

  • Medicinal chemistry
  • Prodrugs
  • Drug design
  • Antiviral agents
  • Meta-thesis
  • Phosphonate synthons
  • Acyclonucleoside phosphonates
  • N-HETEROCYCLIC CARBENES
  • RING-CLOSING METATHESIS
  • ACYCLIC NUCLEOSIDE PHOSPHONATES
  • RUTHENIUM CATALYSTS
  • ANTIVIRAL ACTIVITY
  • NUCLEOPHILIC CARBENE
  • LIGANDS
  • COMPLEXES
  • EFFICIENT
  • BEARING

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