Literature DB >> 24151037

Catalytic enantioselective synthesis of functionalized tropanes reveals novel inhibitors of hedgehog signaling.

Rishikesh Narayan1, Jonathan O Bauer, Carsten Strohmann, Andrey P Antonchick, Herbert Waldmann.   

Abstract

Dipolar cycloaddition: A highly efficient copper(I)-catalyzed enantioselective [3+2] cycloaddition reaction of 1,3-fused cyclic azomethine ylides and nitroalkenes has been developed. This method provides access to functionalized tropane scaffolds with several quaternary and tertiary stereocenters in a single step under mild reaction conditions.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; cycloaddition; hedgehog pathway; nitroalkenes; tropanes

Mesh：

Substances：

Year:  2013        PMID： 24151037     DOI： 10.1002/anie.201307392

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  7 in total

Review 1.  Counting on natural products for drug design.

Authors:  Tiago Rodrigues; Daniel Reker; Petra Schneider; Gisbert Schneider
Journal:  Nat Chem       Date:  2016-04-25       Impact factor: 24.427

2.  Intramolecular Hydrogen Bond Activation: Thiourea-Organocatalyzed Enantioselective 1,3-Dipolar Cycloaddition of Salicylaldehyde-Derived Azomethine Ylides with Nitroalkenes.

Authors:  Francisco Esteban; Wioleta Cieślik; Enrique M Arpa; Andrea Guerrero-Corella; Sergio Díaz-Tendero; Josefina Perles; José A Fernández-Salas; Alberto Fraile; José Alemán
Journal:  ACS Catal       Date:  2018-01-31       Impact factor: 13.084

3.  Stereoselective Synthesis of Tropanes via a 6π-Electrocyclic Ring-Opening/ Huisgen [3+2]-Cycloaddition Cascade of Monocyclopropanated Heterocycles.

Authors:  Carina M Sonnleitner; Saerom Park; Robert Eckl; Thomas Ertl; Oliver Reiser
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-18       Impact factor: 15.336

4.  Asymmetric Synthesis of Nortropanes via Rh-Catalyzed Allylic Arylation.

Authors:  Yan Zhang; F Wieland Goetzke; Kirsten E Christensen; Stephen P Fletcher
Journal:  ACS Catal       Date:  2022-07-12       Impact factor: 13.700

5.  Enantioselective 1,3-Dipolar Cycloaddition Using (Z)-α-Amidonitroalkenes as a Key Step to the Access to Chiral cis-3,4-Diaminopyrrolidines.

Authors:  Eduardo García-Mingüens; Marcos Ferrándiz-Saperas; M de Gracia Retamosa; Carmen Nájera; Miguel Yus; José M Sansano
Journal:  Molecules       Date:  2022-07-18       Impact factor: 4.927

6.  Synthesis of 20-Membered Macrocyclic Pseudo-Natural Products Yields Inducers of LC3 Lipidation.

Authors:  Georg Niggemeyer; Anastasia Knyazeva; Raphael Gasper; Dale Corkery; Pia Bodenbinder; Julian J Holstein; Sonja Sievers; Yao-Wen Wu; Herbert Waldmann
Journal:  Angew Chem Int Ed Engl       Date:  2022-01-25       Impact factor: 16.823

7.  Catalytic enantioselective 1,3-dipolar cycloadditions of azomethine ylides for biology-oriented synthesis.

Authors:  Rishikesh Narayan; Marco Potowski; Zhi-Jun Jia; Andrey P Antonchick; Herbert Waldmann
Journal:  Acc Chem Res       Date:  2014-03-22       Impact factor: 22.384
  7 in total

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