Literature DB >> 21506209

Dearomatization strategies in the synthesis of complex natural products.

Stéphane P Roche1, John A Porco.   

Abstract

Evolution in the field of the total synthesis of natural products has led to exciting developments over the last decade. Numerous chemoselective and enantioselective methodologies have emerged from total syntheses, resulting in efficient access to many important natural product targets. This Review highlights recent developments concerning dearomatization, a powerful strategy for the total synthesis of architecturally complex natural products wherein planar, aromatic scaffolds are converted to three-dimensional molecular architectures.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2011        PMID: 21506209      PMCID: PMC4136767          DOI: 10.1002/anie.201006017

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


  153 in total

1.  Regioselective synthesis of the bridged tricyclic core of Garcinia natural products via intramolecular aryl acrylate cycloadditions.

Authors:  Eric J Tisdale; Chinmay Chowdhury; Binh G Vong; Hongmei Li; Emmanuel A Theodorakis
Journal:  Org Lett       Date:  2002-03-21       Impact factor: 6.005

Review 2.  Chemistry and biology of biosynthetic Diels-Alder reactions.

Authors:  Emily M Stocking; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2003-07-14       Impact factor: 15.336

3.  Asymmetric syntheses of (-)-mitorubrin and related azaphilone natural products.

Authors:  Jianglong Zhu; John A Porco
Journal:  Org Lett       Date:  2006-10-26       Impact factor: 6.005

4.  Nucleophilic dearomatizing (DNAr) reactions of aromatic C,H-systems. A mature paradigm in organic synthesis.

Authors:  Fernando López Ortiz; María José Iglesias; Ignacio Fernandez; Carmen M Andújar Sanchez; Gloria Ruiz Gómez
Journal:  Chem Rev       Date:  2007-05       Impact factor: 60.622

5.  Highly diastereoselective synthesis of orthoquinone monoketals through lambda3-iodane-mediated oxidative dearomatization of phenols.

Authors:  Laurent Pouységu; Stefan Chassaing; Delphine Dejugnac; Anne-Marie Lamidey; Karinne Miqueu; Jean-Marc Sotiropoulos; Stéphane Quideau
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Mechanism of enzymatic Birch reduction: stereochemical course and exchange reactions of benzoyl-CoA reductase.

Authors:  Bärbel Thiele; Oliver Rieder; Bernard T Golding; Michael Müller; Matthias Boll
Journal:  J Am Chem Soc       Date:  2008-10-01       Impact factor: 15.419

7.  Regiospecific and stereoselective syntheses of (+/-) morphine, codeine, and thebaine via a highly stereocontrolled intramolecular 4 + 2 cycloaddition leading to a phenanthrofuran system.

Authors:  Gilbert Stork; Ayako Yamashita; Julian Adams; Gary R Schulte; Richard Chesworth; Yoji Miyazaki; Jay J Farmer
Journal:  J Am Chem Soc       Date:  2009-08-19       Impact factor: 15.419

8.  Direct coupling of indoles with carbonyl compounds: short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families.

Authors:  Phil S Baran; Jeremy M Richter
Journal:  J Am Chem Soc       Date:  2004-06-23       Impact factor: 15.419

9.  A synthesis of the carbon skeleton of maoecrystal V.

Authors:  Paul J Krawczuk; Niklas Schöne; Phil S Baran
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005

10.  Oxidative Friedel-Crafts reaction and its application to the total syntheses of Amaryllidaceae alkaloids.

Authors:  Kimiaka C Guérard; Cyrille Sabot; Léanne Racicot; Sylvain Canesi
Journal:  J Org Chem       Date:  2009-03-06       Impact factor: 4.354

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  74 in total

1.  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

2.  Shaping Molecular Landscapes: Recent Advances, Opportunities, and Challenges in Dearomatization.

Authors:  Christopher J Huck; David Sarlah
Journal:  Chem       Date:  2020-07-01       Impact factor: 22.804

3.  De Novo Synthesis of the DEF-Ring Stereotriad Core of the Veratrum Alkaloids.

Authors:  Matthew A Horwitz; Jacob G Robins; Jeffrey S Johnson
Journal:  J Org Chem       Date:  2020-04-30       Impact factor: 4.354

4.  Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods.

Authors:  Hem Raj Khatri; Nolan Carney; Ryan Rutkoski; Bijay Bhattarai; Pavel Nagorny
Journal:  European J Org Chem       Date:  2020-01-01

5.  Phenolic Oxidation Using H2O2 via in Situ Generated para-Quinone Methides for the Preparation of para-Spiroepoxydienones.

Authors:  Michael F McLaughlin; Elisabetta Massolo; Thomas A Cope; Jeffrey S Johnson
Journal:  Org Lett       Date:  2019-07-30       Impact factor: 6.005

6.  Photocatalytic Oxidative Dearomatization of Orcinaldehyde Derivatives.

Authors:  Summer A Baker Dockrey; Alison R H Narayan
Journal:  Org Lett       Date:  2020-04-15       Impact factor: 6.005

7.  Total synthesis of maoecrystal V: early-stage C-H functionalization and lactone assembly by radical cyclization.

Authors:  Ping Lu; Zhenhua Gu; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2013-09-23       Impact factor: 15.419

8.  Nickel-Catalyzed Dearomative trans-1,2-Carboamination.

Authors:  Lucas W Hernandez; Ulrich Klöckner; Jola Pospech; Lilian Hauss; David Sarlah
Journal:  J Am Chem Soc       Date:  2018-03-23       Impact factor: 15.419

9.  Whole-cell biocatalysis platform for gram-scale oxidative dearomatization of phenols.

Authors:  Summer A Baker Dockrey; Tyler J Doyon; Jonathan C Perkins; Alison R H Narayan
Journal:  Chem Biol Drug Des       Date:  2018-11-28       Impact factor: 2.817

10.  Gallium(III)-catalyzed cycloisomerization approach to the diterpenoid alkaloids: construction of the core structure for the hetidines and hetisines.

Authors:  Amy M Hamlin; Felipe de Jesus Cortez; David Lapointe; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-26       Impact factor: 15.336

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