Synthesis of L-cyclopentenyl nucleosides using ring-closing metathesis and palladium-mediated allylic alkylation methodologies

L A Agrofoglio, F Amblard, Steven Patrick Nolan, S Charamon, I Gillaizeau, T A Zevaco, P Guenot

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

The enantiomeric synthesis of L-cyclopentenyl nucleosides is described. The key intermediate (+)-cyclopentenyl alcohol (8) was prepared from methyl-alpha-D-galactopyranoside 1 using a ring closing metathesis reaction. Transformation of the allylic alcohol 8 into the allylic acetate (9) or carbonate (10), allows their coupling with purine and pyrimidine bases under Pd(0)-catalyzed Tsuji-Trost allylic alkylation's to yield 12a-c. The Pd catalyzed reaction was found to require the use of AlEt3. (C) 2004 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)8397-8404
Number of pages8
JournalTetrahedron
Volume60
Issue number38
DOIs
Publication statusPublished - 13 Sept 2004

Keywords

  • metathesis
  • palladium
  • nucleosides
  • allylic alkylation
  • CARBOCYCLIC NUCLEOSIDES
  • ENANTIOSELECTIVE SYNTHESIS
  • OLEFIN METATHESIS
  • CLOSURE METATHESIS
  • ANTIVIRAL ACTIVITY
  • CROSS-METATHESIS
  • ANALOGS
  • VIRUS
  • COMPLEXES
  • (-)-ARISTEROMYCIN

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