Literature DB >> 20625519

A greener enantioselective synthesis of the antiviral agent North-methanocarbathymidine (N-MCT) from 2-deoxy-d-ribose.

Olaf R Ludek1, Victor E Marquez.   

Abstract

An enantioselective synthesis of suitably protected (1R,2S,4S,5S)-4-amino-1-(hydroxymethyl)bicyclo[3.1.0]hexan-2-ol, a key starting material for the synthesis of conformationally locked carbocyclic nucleosides, including the antiviral active North-methanocarba thymidine, is reported. Starting from 2-deoxyribose the target Boc-protected amine was prepared in 33% overall yield under condition that are ecologically friendlier than previous methods.

Entities:  

Year:  2009        PMID： 20625519      PMCID： PMC2900805          DOI： 10.1016/j.tet.2009.08.035

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  16 in total

1.  An efficient synthesis of novel carbocyclic nucleosides with use of ring-closing metathesis from D-lactose.

Authors:  Joon Hee Hong; Myung Jung Shim; Bong Oh Ro; Ok Hyun Ko
Journal:  J Org Chem       Date:  2002-09-20       Impact factor: 4.354

2.  Diastereoselectivity in Organometallic Additions to the Carbonyl Group of Protected Erythrulose Derivatives.

Authors:  J. Alberto Marco; Miguel Carda; Florenci González; Santiago Rodríguez; Encarna Castillo; Juan Murga
Journal:  J Org Chem       Date:  1998-02-06       Impact factor: 4.354

3.  Synthesis and antiviral activity of acyclic nucleosides with a 3(S),5-dihydroxypentyl or 4(R)-methoxy-3(S),5-dihydroxypentyl side chain.

Authors:  F Vandendriessche; R Snoeck; G Janssen; J Hoogmartens; A Van Aerschot; E De Clercq; P Herdewijn
Journal:  J Med Chem       Date:  1992-04-17       Impact factor: 7.446

4.  Enantioselective synthesis of bicyclo[3.1.0]hexane carbocyclic nucleosides via a lipase-catalyzed asymmetric acetylation. Characterization of an unusual acetal byproduct.

Authors:  Yuichi Yoshimura; Hyung R Moon; Yongseok Choi; Victor E Marquez
Journal:  J Org Chem       Date:  2002-08-23       Impact factor: 4.354

5.  Preparative and stereoselective synthesis of the versatile intermediate for carbocyclic nucleosides: effects of the bulky protecting groups to enforce facial selectivity.

Authors:  Won Jun Choi; Hyung Ryong Moon; Hea Ok Kim; Byul Nae Yoo; Jeong A Lee; Dae Hong Shin; Lak Shin Jeong
Journal:  J Org Chem       Date:  2004-04-02       Impact factor: 4.354

Review 6.  The history of N-methanocarbathymidine: the investigation of a conformational concept leads to the discovery of a potent and selective nucleoside antiviral agent.

Authors:  Victor E Marquez; Stephen H Hughes; Shizuko Sei; Riad Agbaria
Journal:  Antiviral Res       Date:  2006-05-06       Impact factor: 10.103

7.  Cell line dependency for antiviral activity and in vivo efficacy of N-methanocarbathymidine against orthopoxvirus infections in mice.

Authors:  Donald F Smee; Miles K Wandersee; Kevin W Bailey; Min-Hui Wong; Chung K Chu; Srinivas Gadthula; Robert W Sidwell
Journal:  Antiviral Res       Date:  2006-05-05       Impact factor: 10.103

8.  Activity and mechanism of action of N-methanocarbathymidine against herpesvirus and orthopoxvirus infections.

Authors:  Mark N Prichard; Kathy A Keith; Debra C Quenelle; Earl R Kern
Journal:  Antimicrob Agents Chemother       Date:  2006-04       Impact factor: 5.938

9.  Potent antiviral activity of north-methanocarbathymidine against Kaposi's sarcoma-associated herpesvirus.

Authors:  Weimin Zhu; Angela Burnette; Dorjbal Dorjsuren; Paula E Roberts; Mahmoud Huleihel; Robert H Shoemaker; Victor E Marquez; Riad Agbaria; Shizuko Sei
Journal:  Antimicrob Agents Chemother       Date:  2005-12       Impact factor: 5.938

10.  Metabolic pathways of N-methanocarbathymidine, a novel antiviral agent, in native and herpes simplex virus type 1 infected Vero cells.

Authors:  Livnat Zalah; Mahmoud Huleihel; Esther Manor; Alexander Konson; Harry Ford; Victor E Marquez; David G Johns; Riad Agbaria
Journal:  Antiviral Res       Date:  2002-07       Impact factor: 10.103
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  3 in total

1.  Efficient synthesis of fluorescent alkynyl C-nucleosides via Sonogashira coupling for the preparation of DNA-based polyfluorophores.

Authors:  Dominik K Kölmel; Luzi J Barandun; Eric T Kool
Journal:  Org Biomol Chem       Date:  2016-07-06       Impact factor: 3.876

2.  Synthesis of Thienamycin methyl ester from 2-deoxy-D-ribose via Kinugasa reaction.

Authors:  Magdalena Soluch; Barbara Grzeszczyk; Olga Staszewska-Krajewska; Marek Chmielewski; Bartłomiej Furman
Journal:  J Antibiot (Tokyo)       Date:  2015-10-28       Impact factor: 2.649

Review 3.  Highlights in antiviral drug research: antivirals at the horizon.

Authors:  Erik De Clercq
Journal:  Med Res Rev       Date:  2012-05-02       Impact factor: 12.944
  3 in total

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