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Current Topics in Medicinal Chemistry


ISSN (Print): 1568-0266
ISSN (Online): 1873-4294

Olefin Metathesis Route to Antiviral Nucleosides

Author(s): Luigi A. Agrofoglio and Steven P. Nolan

Volume 5, Issue 15, 2005

Page: [1541 - 1558] Pages: 18

DOI: 10.2174/156802605775009739

Price: $65


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.

Keywords: neplanocin A, chemicoenzymatic approach, anti-cytomegalovirus activity, D-isoascorbic acid, ACYCLONUCLEOSIDE, Ortho-ester Claisen rearrangement, crotylthymine

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