Efficient synthesis of various acycloalkenyl derivatives of pyrimidine using cross-metathesis and Pd(0) methodologies

F Amblard, Steven Patrick Nolan, RF Schinazi, LA Agrofoglio

Research output: Contribution to journalArticlepeer-review

43 Citations (Scopus)

Abstract

Novel acyclonucleosides (9a-d, 10a-d, 18a,b and 19a,b) have been prepared using Pd(0) and cross-metathesis methodologies. The allylic N-alkylation under Tsuji-Trost conditions was used to introduce the nucleobase, while the Suzuki-Miyaura reaction afforded C-5 substituted uracil analogues. The cross-metathesis performed with a ruthenium catalyst was used to provide new acycloalkenyl nucleosides. The antiviral activities of all final compounds have been evaluated. (C) 2004 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)537-544
Number of pages8
JournalTetrahedron
Volume61
Issue number3
DOIs
Publication statusPublished - 17 Jan 2005

Keywords

  • ACYCLIC NUCLEOSIDE ANALOGS
  • ANTI-DNA VIRUS
  • OLEFIN METATHESIS
  • ORGANOBORON DERIVATIVES
  • ANTIVIRAL ACTIVITIES
  • COUPLING REACTION
  • 9-(2-HYDROXYETHOXYMETHYL)GUANINE
  • INHIBITION
  • CHEMISTRY
  • AGENT

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