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Progress in Chemistry 2010, Vol. 22 Issue (08): 1583-1590 Previous Articles   Next Articles

• Review •

Application of Metathesis in Synthesis of Nucleosides Analogs

Guan Zhu1  Zhang Yongmin2*   

  1. (1. Peking University Health Science Center, State Key Laboratory of Natural and Biomimetic Drugs, Beijing 100191, China; 2 Institut Parisien de Chimie Moléculaire, UMR CNRS 7201, Université Pierre & Marie Curie-Paris 6, 4 Place Jussieu, 75005 Paris, France)
  • Received: Revised: Online: Published:
  • Contact: Zhang Yongmin E-mail:yongmin.zhang@upmc.fr
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Nucleosides analogs may participate and interfere in some way with DNA or RNA replication,transcription or reverse transcription in bacteria or virus, which made them potential antibacterial or antivirus drugs. Some natural nucleosides behave biologically active in vitro, however, instability to enzyme and poor selectivity in vivo restrict their application in medicinal field. Synthesis of chemically modified nucleosides and their derivatives as biologically active molecules has been an important topic in nucleic acid medicinal chemistry. Metathesis reaction, an inter- or intramolecular exchange reaction of alkylidene catalyzed by metal-carbene complex, makes the synthesis of nucleosides analogs go into a new stage, and becomes one of the main routes for the synthesis of nucleosides analogs. Driven by the discovery and improvement of metathesis catalysts, such as Schrock catalysts, Grubbs catalysts etc., olefin-metathesis reactions, especially olefin ring-closing metathesis (RCM) and cross-metathesis (CM) reactions, are widely used in constructing functionalized sugars (or pseudo sugars) in nucleosides analogs structures or connecting two nucleosides to form nucleotide dimers or trimers. Application of olefin metathesis reaction in the synthesis of nucleosides analogs, including carbocyclic nucleosides, 2’, 3’-dideoxynucleosides, acyclonucleosides, polycyclic nucleosides, and nucleosides or nucleotides dimers or trimers, is reviewed in this paper.

Contents: 
1 Introduction 
1. 1 The development of nucleoside chemistry in medicinal chemistry 
1. 2 Metathesis reaction and its catalysts 
2 Application of olefin metathesis in the synthesis of nucleosides analogs 
2. 1 Carbocyclic nucleosides 
2. 2 2’, 3’-Didehydro-2’, 3’-dideoxynucleosides
2. 3 Acyclonucleosides 
2. 4 Polycyclic nucleosides 
2. 5 Nucleoside or nucleotide dimers or trimers 
3 Outlook

Key words: nucleosides, metathesis, synthesis

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