Literature DB >> 21365707

Development of a concise synthesis of (-)-oseltamivir (Tamiflu).

Barry M Trost1, Ting Zhang.   

Abstract

We report a full account of our work towards the development of an eight-step synthesis of anti-influenza drug (-)-oseltamivir (Tamiflu) from commercially available starting materials. The final synthetic route proceeds with an overall yield of 30 %. Key transformations include a novel palladium-catalyzed asymmetric allylic alkylation reaction (Pd-AAA) as well as a rhodium-catalyzed chemo-, regio-, and stereoselective aziridination reaction.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2011        PMID: 21365707      PMCID: PMC3079541          DOI: 10.1002/chem.201003454

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  42 in total

1.  Advances in nitrogen transfer reactions involving aziridines.

Authors:  Iain D G Watson; Lily Yu; Andrei K Yudin
Journal:  Acc Chem Res       Date:  2006-03       Impact factor: 22.384

2.  A synthesis of Tamiflu by using a barium-catalyzed asymmetric Diels-Alder-type reaction.

Authors:  Kenzo Yamatsugu; Liang Yin; Shin Kamijo; Yasuaki Kimura; Motomu Kanai; Masakatsu Shibasaki
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  Sugar-based synthesis of Tamiflu and its inhibitory effects on cell secretion.

Authors:  Jimei Ma; Yanying Zhao; Simon Ng; Jing Zhang; Jing Zeng; Aung Than; Peng Chen; Xue-Wei Liu
Journal:  Chemistry       Date:  2010-03-09       Impact factor: 5.236

4.  Ring-closing metathesis-based synthesis of (3R,4R,5S)-4-acetylamino-5-amino-3-hydroxy- cyclohex-1-ene-carboxylic acid ethyl ester: a functionalized cycloalkene skeleton of GS4104.

Authors:  Xin Cong; Zhu-Jun Yao
Journal:  J Org Chem       Date:  2006-07-07       Impact factor: 4.354

5.  Palladium-catalyzed DYKAT of butadiene monoepoxide: enantioselective total synthesis of (+)-DMDP, (-)-bulgecinine, and (+)-broussonetine G.

Authors:  Barry M Trost; Daniel B Horne; Michael J Woltering
Journal:  Chemistry       Date:  2006-08-25       Impact factor: 5.236

6.  Organocatalytic Michael addition of aldehydes to protected 2-amino-1-nitroethenes: the practical syntheses of oseltamivir (Tamiflu) and substituted 3-aminopyrrolidines.

Authors:  Shaolin Zhu; Shouyun Yu; You Wang; Dawei Ma
Journal:  Angew Chem Int Ed Engl       Date:  2010-06-21       Impact factor: 15.336

7.  Second generation catalytic asymmetric synthesis of Tamiflu: allylic substitution route.

Authors:  Tsuyoshi Mita; Nobuhisa Fukuda; Francesc X Roca; Motomu Kanai; Masakatsu Shibasaki
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

8.  Aza-Michael addition of nosyloxycarbamates to 2-(trifluoromethyl)acrylates.

Authors:  Daniele Colantoni; Stefania Fioravanti; Lucio Pellacani; Paolo A Tardella
Journal:  Org Lett       Date:  2004-01-22       Impact factor: 6.005

9.  Palladium-catalyzed DYKAT of vinyl epoxides: enantioselective total synthesis and assignment of the configuration of (+)-Broussonetine G.

Authors:  Barry M Trost; Daniel B Horne; Michael J Woltering
Journal:  Angew Chem Int Ed Engl       Date:  2003-12-15       Impact factor: 15.336

10.  Symmetry-based design for the chemoenzymatic synthesis of oseltamivir (Tamiflu) from ethyl benzoate.

Authors:  Bradford Sullivan; Ignacio Carrera; Melissa Drouin; Tomas Hudlicky
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

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  3 in total

1.  Pd and Mo Catalyzed Asymmetric Allylic Alkylation.

Authors:  Barry M Trost
Journal:  Org Process Res Dev       Date:  2012-01-13       Impact factor: 3.317

2.  Polygonum cuspidatum and its active components inhibit replication of the influenza virus through toll-like receptor 9-induced interferon beta expression.

Authors:  Chao-Jen Lin; Hui-Ju Lin; Ter-Hsin Chen; Yu-An Hsu; Chin-San Liu; Guang-Yuh Hwang; Lei Wan
Journal:  PLoS One       Date:  2015-02-06       Impact factor: 3.240

3.  Enantioselective construction of C-chiral allylic sulfilimines via the iridium-catalyzed allylic amination with S,S-diphenylsulfilimine: asymmetric synthesis of primary allylic amines.

Authors:  Rebecca L Grange; Elizabeth A Clizbe; Emma J Counsell; P Andrew Evans
Journal:  Chem Sci       Date:  2014-09-08       Impact factor: 9.825

  3 in total

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