Literature DB >> 21124474

Organocatalytic cascade reactions as a new tool in total synthesis.

Christoph Grondal1, Matthieu Jeanty, Dieter Enders.   

Abstract

The total synthesis of natural products and biologically active compounds, such as pharmaceuticals and agrochemicals, has reached an extraordinary level of sophistication. We are, however, still far away from the 'ideal synthesis' and the state of the art is still frequently hampered by lengthy protecting-group strategies and costly purification procedures derived from the step-by-step protocols. In recent years several new criteria have been brought forward to solve these problems and to improve total synthesis: atom, step and redox economy or protecting-group-free synthesis. Over the past decade the research area of organocatalysis has rapidly grown to become a third pillar of asymmetric catalysis standing next to metal and biocatalysis, thus paving the way for a new and powerful strategy that can help to address these issues - organocatalytic cascade reactions. In this Review we present the first applications of such asymmetric organocascade reactions to the total synthesis of natural products.

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Year:  2010        PMID: 21124474     DOI: 10.1038/nchem.539

Source DB:  PubMed          Journal:  Nat Chem        ISSN: 1755-4330            Impact factor:   24.427


  55 in total

1.  A powerful Brønsted acid catalyst for the organocatalytic asymmetric transfer hydrogenation of imines.

Authors:  Sebastian Hoffmann; Abdul Majeed Seayad; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2005-12-01       Impact factor: 15.336

Review 2.  Organocatalysis by N-heterocyclic carbenes.

Authors:  Dieter Enders; Oliver Niemeier; Alexander Henseler
Journal:  Chem Rev       Date:  2007-10-23       Impact factor: 60.622

3.  Redox economy in organic synthesis.

Authors:  Noah Z Burns; Phil S Baran; Reinhard W Hoffmann
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 4.  Chemistry and biology of mycotoxins and related fungal metabolites.

Authors:  Stefan Bräse; Arantxa Encinas; Julia Keck; Carl F Nising
Journal:  Chem Rev       Date:  2009-09       Impact factor: 60.622

Review 5.  The economies of synthesis.

Authors:  Timothy Newhouse; Phil S Baran; Reinhard W Hoffmann
Journal:  Chem Soc Rev       Date:  2009-08-21       Impact factor: 54.564

6.  Concise synthesis of ricciocarpin A and discovery of a more potent analogue.

Authors:  Anna Michrowska; Benjamin List
Journal:  Nat Chem       Date:  2009-05-22       Impact factor: 24.427

7.  Enantioselective organo-cascade catalysis.

Authors:  Yong Huang; Abbas M Walji; Catharine H Larsen; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2005-11-02       Impact factor: 15.419

8.  Enantioselective organocatalytic formal [3 + 3]-cycloaddition of alpha,beta-unsaturated aldehydes and application to the asymmetric synthesis of (-)-isopulegol hydrate and (-)-cubebaol.

Authors:  Bor-Cherng Hong; Ming-Fun Wu; Hsing-Chang Tseng; Ju-Hsiou Liao
Journal:  Org Lett       Date:  2006-05-25       Impact factor: 6.005

Review 9.  Function-oriented synthesis, step economy, and drug design.

Authors:  Paul A Wender; Vishal A Verma; Thomas J Paxton; Thomas H Pillow
Journal:  Acc Chem Res       Date:  2007-12-27       Impact factor: 22.384

10.  Nine-step enantioselective total synthesis of (+)-minfiensine.

Authors:  Spencer B Jones; Bryon Simmons; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2009-09-30       Impact factor: 15.419

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  109 in total

1.  Crystalline 1H-1,2,3-triazol-5-ylidenes: new stable mesoionic carbenes (MICs).

Authors:  Gregorio Guisado-Barrios; Jean Bouffard; Bruno Donnadieu; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2010-06-28       Impact factor: 15.336

2.  Domino reactions: More than just a game.

Authors:  Thomas Broja; Patrick J W Fuchs; Kirsten Zeitler
Journal:  Nat Chem       Date:  2015-12       Impact factor: 24.427

3.  Enantioselective synthesis of hindered cyclic dialkyl ethers via catalytic oxa-Michael/Michael desymmetrization.

Authors:  Michael T Corbett; Jeffrey S Johnson
Journal:  Chem Sci       Date:  2013-07-01       Impact factor: 9.825

4.  Collective synthesis of natural products by means of organocascade catalysis.

Authors:  Spencer B Jones; Bryon Simmons; Anthony Mastracchio; David W C MacMillan
Journal:  Nature       Date:  2011-07-13       Impact factor: 49.962

Review 5.  Engineering synthetic recursive pathways to generate non-natural small molecules.

Authors:  Elizabeth A Felnagle; Asha Chaubey; Elizabeth L Noey; Kendall N Houk; James C Liao
Journal:  Nat Chem Biol       Date:  2012-05-17       Impact factor: 15.040

6.  An asymmetric synthesis of 1,2,4-trioxane anticancer agents via desymmetrization of peroxyquinols through a Brønsted acid catalysis cascade.

Authors:  David M Rubush; Michelle A Morges; Barbara J Rose; Douglas H Thamm; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2012-08-07       Impact factor: 15.419

7.  Reaction design: Nature-inspired total synthesis.

Authors:  Laura Furst; Corey R J Stephenson
Journal:  Nat Chem Biol       Date:  2011-08-17       Impact factor: 15.040

8.  A general organocatalyzed Michael-Michael cascade reaction generates functionalized cyclohexenes.

Authors:  Patrick G McGarraugh; Joshua H Jones; Stacey E Brenner-Moyer
Journal:  J Org Chem       Date:  2011-07-08       Impact factor: 4.354

Review 9.  The ever-expanding role of asymmetric covalent organocatalysis in scalable, natural product synthesis.

Authors:  Mikail E Abbasov; Daniel Romo
Journal:  Nat Prod Rep       Date:  2014-10       Impact factor: 13.423

10.  Natural product synthesis at the interface of chemistry and biology.

Authors:  Jiyong Hong
Journal:  Chemistry       Date:  2014-07-10       Impact factor: 5.236

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