Literature DB >> 15232003

Contiguous stereogenic quaternary carbons: a daunting challenge in natural products synthesis.

Emily A Peterson1, Larry E Overman.   

Abstract

One element of structure that invariably increases the difficulty of a chemical synthesis is the presence in the target molecule of contiguous all-carbon quaternary stereocenters. This Perspective will examine the most useful transformations and strategies devised recently for directly assembling this structural unit.

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Year:  2004        PMID： 15232003      PMCID： PMC514413          DOI： 10.1073/pnas.0402416101

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  9 in total

1.  Investigation of a dialkylation approach for enantioselective construction of vicinal quaternary stereocenters.

Authors:  S B Hoyt; L E Overman
Journal:  Org Lett       Date:  2000-10-05       Impact factor: 6.005

2.  Enantioselective total synthesis of the cyclotryptamine alkaloid idiospermuline.

Authors:  Larry E Overman; Emily A Peterson
Journal:  Angew Chem Int Ed Engl       Date:  2003-06-06       Impact factor: 15.336

3.  The asymmetric intramolecular Heck reaction in natural product total synthesis.

Authors:  Amy B Dounay; Larry E Overman
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

4.  Enantioselective Construction of Vicinal Stereogenic Quaternary Centers by Dialkylation: Practical Total Syntheses of (+)- and meso-Chimonanthine.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-01       Impact factor: 15.336

5.  Nature knows best: an amazing reaction cascade is uncovered by design and discovery.

Authors:  C H Heathcock
Journal:  Proc Natl Acad Sci U S A       Date:  1996-12-10       Impact factor: 11.205

6.  Biomimetic polyene cyclizations.

Authors:  W S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  1976-01       Impact factor: 15.336

7.  Highly selective entry to the azadirachtin skeleton via a Claisen rearrangement/radical cyclization sequence.

Authors:  Thomas Durand-Reville; Luca B Gobbi; Brian Lawrence Gray; Steven V Ley; James S Scott
Journal:  Org Lett       Date:  2002-10-31       Impact factor: 6.005

8.  Enantioselective total synthesis of quadrigemine C and psycholeine.

Authors:  Alec D Lebsack; J T Link; Larry E Overman; Brian A Stearns
Journal:  J Am Chem Soc       Date:  2002-08-07       Impact factor: 15.419

9.  Catalytic asymmetric synthesis of all-carbon quaternary stereocenters.

Authors:  Christopher J Douglas; Larry E Overman
Journal:  Proc Natl Acad Sci U S A       Date:  2004-01-14       Impact factor: 11.205
  9 in total
  36 in total

Review 1.  Recent Advances on the Total Syntheses of Communesin Alkaloids and Perophoramidine.

Authors:  Barry M Trost; Maksim Osipov
Journal:  Chemistry       Date:  2015-09-10       Impact factor: 5.236

2.  Enantioselective construction of spirocyclic oxindolic cyclopentanes by palladium-catalyzed trimethylenemethane-[3+2]-cycloaddition.

Authors:  Barry M Trost; Nicolai Cramer; Steven M Silverman
Journal:  J Am Chem Soc       Date:  2007-09-20       Impact factor: 15.419

3.  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

4.  Asymmetric palladium-catalyzed intramolecular alpha-arylation of aldehydes.

Authors:  Jorge García-Fortanet; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates.

Authors:  Pavel Starkov; Jared T Moore; Douglas C Duquette; Brian M Stoltz; Ilan Marek
Journal:  J Am Chem Soc       Date:  2017-07-07       Impact factor: 15.419

6.  Enantio- and Diastereoselective Synthesis of Functionalized Carbocycles by Cu-Catalyzed Borylative Cyclization of Alkynes with Ketones.

Authors:  Joseph M Zanghi; Shuang Liu; Simon J Meek
Journal:  Org Lett       Date:  2019-06-14       Impact factor: 6.005

7.  Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-11       Impact factor: 15.336

8.  Synthesis of the tetracyclic core of exiguaquinol.

Authors:  Gregg M Schwarzwalder; Sarah E Steinhardt; Hung V Pham; K N Houk; Christopher D Vanderwal
Journal:  Org Lett       Date:  2013-11-12       Impact factor: 6.005

Review 9.  Axial preferences in allylation reactions via the Zimmerman-Traxler transition state.

Authors:  Tom Mejuch; Noga Gilboa; Eric Gayon; Hao Wang; K N Houk; Ilan Marek
Journal:  Acc Chem Res       Date:  2013-05-14       Impact factor: 22.384

10.  Palladium-catalyzed asymmetric dearomatization of naphthalene derivatives.

Authors:  Jorge García-Fortanet; Florian Kessler; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-05-20       Impact factor: 15.419
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