Literature DB >> 15535045

Recent advances in the synthesis of the carbocyclic nucleosides as potential antiviral agents.

Lak Shin Jeong1, Jeong A Lee.   

Abstract

Compared with 4'-oxonucleosides, there have been far fewer systematic structure-activity relationship studies on carbocyclic nucleosides as antiviral and antitumour agents. This is mainly because of the synthetic problems in preparing the carbasugars. However, the recent discovery of the ring-closing metathesis (RCM) (a powerful tool for the preparation of 5-membered carbasugar via C-C bond formation) has made it possible to synthesize the key carbasugars to a preparative scale. This review summarizes the asymmetric syntheses of carbasugars and carbocyclic nucleosides, using an RCM reaction as a key step. Furthermore, the review includes valuable information for designing and synthesizing novel carbocyclic nucleosides.

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Year:  2004        PMID: 15535045     DOI: 10.1177/095632020401500502

Source DB:  PubMed          Journal:  Antivir Chem Chemother        ISSN: 0956-3202


  8 in total

1.  Syntheses of carbocyclic aminonucleosides and (-)-epi-4'-carbocyclic puromycin: Application of palladium(0)/indium iodide-allylations and tethered aminohydroxylations.

Authors:  Cara Cesario; Lawrence P Tardibono; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2010-06-09       Impact factor: 2.415

Review 2.  Dynamic kinetic resolution of Vince lactam catalyzed by γ-lactamases: a mini-review.

Authors:  Shaozhou Zhu; Guojun Zheng
Journal:  J Ind Microbiol Biotechnol       Date:  2018-10-23       Impact factor: 3.346

3.  Synthesis of cyclopentanyl carbocyclic 5-fluorocytosine ((-)-5-fluorocarbodine) using a facially selective hydrogenation approach.

Authors:  Jong Hyun Cho; Franck Amblard; Steven J Coats; Raymond F Schinazi
Journal:  J Org Chem       Date:  2012-12-26       Impact factor: 4.354

4.  Cyclopropanation of nitroso Diels-Alder cycloadducts and application to the synthesis of a 2',3'-methano carbocyclic nucleoside.

Authors:  Cheng Ji; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2010-07-01       Impact factor: 2.415

Review 5.  The nitrosocarbonyl hetero-Diels-Alder reaction as a useful tool for organic syntheses.

Authors:  Brian S Bodnar; Marvin J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-21       Impact factor: 15.336

6.  Syntheses of new spirocarbocyclic nucleoside analogs using iminonitroso Diels-Alder reactions.

Authors:  Weimin Lin; Anuradha Gupta; Kyung Hee Kim; David Mendel; Marvin J Miller
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

7.  Diastereoselective synthesis of a spironoraristeromycin using an acylnitroso Diels-Alder reaction.

Authors:  Weimin Lin; Kristopher G Virga; Kyung-Hee Kim; Jaroslav Zajicek; David Mendel; Marvin J Miller
Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354

8.  Syntheses of carbocyclic uracil polyoxin C analogs: application of Pd(0)/InI-allylation of 4-acetoxy-2-azetidinone.

Authors:  Cara Cesario; Marvin J Miller
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

  8 in total

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