Preparation of acyclo nucleoside phosphonate analogues based on cross-metathesis

Hiroki Kumamoto, Dimitri Topalis, Julie Broggi, Ugo Pradere, Vincent Roy, Sabine Berteina-Raboin, Steven Patrick Nolan, Dominique Deville-Bonne, Graciela Andrei, Robert Snoeck, Daniel Garin, Jean-Marc Crance, Luigi A. Agrofoglio

Research output: Contribution to journalArticlepeer-review

44 Citations (Scopus)

Abstract

In our on-going program targeting anti-pox activity, we report here the synthesis of hitherto unknown acyclic nucleoside phosphonates using olefin cross-metathesis (CM) as a key assembly step. Modification at the C-5 position of the uracil moiety was performed under optimized Pd(0)-catalyzed Stille cross-coupling conditions. None of the obtained compounds were active against poxviruses, nor do they exhibit any toxicity. (c) 2008 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)3517-3526
Number of pages10
JournalTetrahedron
Volume64
Issue number16
DOIs
Publication statusPublished - 14 Apr 2008

Keywords

  • RING-CLOSING METATHESIS
  • ANTIVIRAL ACTIVITY
  • OLEFIN METATHESIS
  • CATALYZED HYDROPHOSPHORYLATION
  • CIDOFOVIR
  • DERIVATIVES
  • LIGANDS
  • REARRANGEMENT
  • HETEROCYCLES
  • NUCLEOTIDES

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