Literature DB >> 12945759

Enantioselective synthesis of BMS-204352 (MaxiPost) using N-fluoroammonium salts of cinchona alkaloids (F-CA-BF4).

Ludivine Zoute1, Christophe Audouard, Jean-Christophe Plaquevent, Dominique Cahard.   

Abstract

The enantioselective synthesis of a potent Maxi-K potassium channel opener (BMS-204352) mediated by N-fluoroammonium salts of cinchona alkaloids is described. Two synthetic pathways were evaluated. An ee as high as 88% was achieved (>99% after a single recrystallisation).

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Year:  2003        PMID： 12945759     DOI： 10.1039/b303113f

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  4 in total

1.  Enantioselective decarboxylative alkylation reactions: catalyst development, substrate scope, and mechanistic studies.

Authors:  Douglas C Behenna; Justin T Mohr; Nathaniel H Sherden; Smaranda C Marinescu; Andrew M Harned; Kousuke Tani; Masaki Seto; Sandy Ma; Zoltán Novák; Michael R Krout; Ryan M McFadden; Jennifer L Roizen; John A Enquist; David E White; Samantha R Levine; Krastina V Petrova; Akihiko Iwashita; Scott C Virgil; Brian M Stoltz
Journal:  Chemistry       Date:  2011-11-14       Impact factor: 5.236

Review 2.  Modern Approaches for Asymmetric Construction of Carbon-Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs.

Authors:  Yi Zhu; Jianlin Han; Jiandong Wang; Norio Shibata; Mikiko Sodeoka; Vadim A Soloshonok; Jaime A S Coelho; F Dean Toste
Journal:  Chem Rev       Date:  2018-04-02       Impact factor: 60.622

3.  DBFOX-Ph/metal complexes: evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones.

Authors:  Takehisa Ishimaru; Norio Shibata; Dhande Sudhakar Reddy; Takao Horikawa; Shuichi Nakamura; Takeshi Toru
Journal:  Beilstein J Org Chem       Date:  2008-05-20       Impact factor: 2.883

4.  Syntheses of fluorooxindole and 2-fluoro-2-arylacetic acid derivatives from diethyl 2-fluoromalonate ester.

Authors:  Antal Harsanyi; Graham Sandford; Dmitri S Yufit; Judith Ak Howard
Journal:  Beilstein J Org Chem       Date:  2014-05-22       Impact factor: 2.883
  4 in total

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