Olefin metathesis route to antiviral nucleosides.
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.
Agrofoglio
Luigi A
LA
ICOA UMR CNRS 6005, BP 6759, 45067 Orleans Cedex 2, France. luigi.agrofoglio@univ-orleans.fr
Nolan
Steven P
SP
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D008982:Molybdenum / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D000998:Antiviral Agents; D009705:Nucleosides; D009942:Organometallic Compounds; D012428:Ruthenium; D008982:Molybdenum