Olefin metathesis route to antiviral nucleosides

LA Agrofoglio, Steven Patrick Nolan

Research output: Other contribution

26 Citations (Scopus)

Abstract

The success of the early nucleoside agents, the toxicity and metabolic instability of many nucleoside analogues and the effects of viral pathogens on public health are driving the design, synthesis and evaluation of new nucleoside analogues. In this context, a powerful reaction has emerged over the past decade that has fundamentally changed the outlook on nucleoside chemistry: the olefin metathesis reaction. This review is designed to give an overview of the synthesis of some nucleosides of biological interest, according to their structural types (e.g., neplanocins and aristeromycin analogues, 2',3'-unsaturated nucleoside analogues, and acyclonucleosides), using metathesis reactions by employing either the alkoxy imido molybdenum catalyst developed by Schrock and various ruthenium carbene catalysts developed by Grubbs, Hoveyda-Grubbs and Nolan.

Original languageEnglish
Volume5
DOIs
Publication statusPublished - Nov 2005

Keywords

  • RING-CLOSING METATHESIS
  • S-ADENOSYLHOMOCYSTEINE HYDROLASE
  • ADENOSYLMETHIONINE-DEPENDENT METHYLTRANSFERASES
  • ACID RELATED-COMPOUNDS
  • BRANCHED CARBOCYCLIC NUCLEOSIDES
  • IMMUNODEFICIENCY-VIRUS INVITRO
  • L-CYCLOPENTENONE DERIVATIVES
  • MEDIATED ALLYLIC ALKYLATION
  • MOUSE L929 CELLS
  • ANTI-DNA VIRUS

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