Literature DB >> 23406520

A highly convergent and efficient synthesis of a macrocyclic hepatitis C virus protease inhibitor BI 201302.

Xudong Wei1, Chutian Shu, Nizar Haddad, Xingzhong Zeng, Nitinchandra D Patel, Zhulin Tan, Jianxiu Liu, Heewon Lee, Sherry Shen, Scot Campbell, Richard J Varsolona, Carl A Busacca, Azad Hossain, Nathan K Yee, Chris H Senanayake.   

Abstract

A highly convergent large scale synthesis of a 15-membered macrocyclic hepatitis C virus (HCV) protease inhibitor BI 201302 was achieved, in which the key features are the practical macrocyclization by Ru-catalyzed ring-closing metathesis (0.1 mol % Grela catalyst, 0.1-0.2 M concentration) and the efficient sulfone-mediated SNAr reaction.

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Year:  2013        PMID: 23406520     DOI: 10.1021/ol303498m

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Sequential C-H Arylation and Enantioselective Hydrogenation Enables Ideal Asymmetric Entry to the Indenopiperidine Core of an 11β-HSD-1 Inhibitor.

Authors:  Xudong Wei; Bo Qu; Xingzhong Zeng; Jolaine Savoie; Keith R Fandrick; Jean-Nicolas Desrosiers; Sergei Tcyrulnikov; Maurice A Marsini; Frederic G Buono; Zhibin Li; Bing-Shiou Yang; Wenjun Tang; Nizar Haddad; Osvaldo Gutierrez; Jun Wang; Heewon Lee; Shengli Ma; Scot Campbell; Jon C Lorenz; Matthias Eckhardt; Frank Himmelsbach; Stefan Peters; Nitinchandra D Patel; Zhulin Tan; Nathan K Yee; Jinhua J Song; Frank Roschangar; Marisa C Kozlowski; Chris H Senanayake
Journal:  J Am Chem Soc       Date:  2016-11-17       Impact factor: 15.419

Review 2.  Macrocyclic drugs and synthetic methodologies toward macrocycles.

Authors:  Xufen Yu; Dianqing Sun
Journal:  Molecules       Date:  2013-05-24       Impact factor: 4.411

3.  Stereoselective synthesis of macrocyclic peptides via a dual olefin metathesis and ethenolysis approach.

Authors:  Shane L Mangold; Robert H Grubbs
Journal:  Chem Sci       Date:  2015-05-21       Impact factor: 9.825

  3 in total

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