Literature DB >> 27779393

Total Synthesis of Swinholide A: An Exposition in Hydrogen-Mediated C-C Bond Formation.

Inji Shin1, Suckchang Hong1, Michael J Krische1.   

Abstract

Diverse hydrogen-mediated C-C couplings enable construction of the actin-binding marine polyketide swinholide A in only 15 steps (longest linear sequence), roughly half the steps required in two prior total syntheses. The redox-economy, chemo- and stereoselectivity embodied by this new class of C-C couplings are shown to evoke a step-change in efficiency.

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Year:  2016        PMID： 27779393      PMCID： PMC5096380          DOI： 10.1021/jacs.6b10645

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  33 in total

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Authors:  K C Nicolaou; Paul G Bulger; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-18       Impact factor: 15.336

Review 4.  Macrocyclization by ring-closing metathesis in the total synthesis of natural products: reaction conditions and limitations.

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Journal:  Angew Chem Int Ed Engl       Date:  2006-09-18       Impact factor: 15.336

5.  Structural basis of swinholide A binding to actin.

Authors:  Vadim A Klenchin; Ryan King; Junichi Tanaka; Gerard Marriott; Ivan Rayment
Journal:  Chem Biol       Date:  2005-03

6.  Synthetic mimetics of actin-binding macrolides: rational design of actin-targeted drugs.

Authors:  Richard D Perrins; Giuseppe Cecere; Ian Paterson; Gerard Marriott
Journal:  Chem Biol       Date:  2008-03

Review 7.  Actin-binding marine macrolides: total synthesis and biological importance.

Authors:  Kap-Sun Yeung; Ian Paterson
Journal:  Angew Chem Int Ed Engl       Date:  2002-12-16       Impact factor: 15.336

8.  Prevention of undesirable isomerization during olefin metathesis.

Authors:  Soon Hyeok Hong; Daniel P Sanders; Choon Woo Lee; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2005-12-14       Impact factor: 15.419

Review 9.  The actin cytoskeleton as a therapeutic target: state of the art and future directions.

Authors:  Adeline Giganti; Evelyne Friederich
Journal:  Prog Cell Cycle Res       Date:  2003

10.  Diastereo- and enantioselective hydrogenative aldol coupling of vinyl ketones: design of effective monodentate TADDOL-like phosphonite ligands.

Authors:  Cisco Bee; Soo Bong Han; Abbas Hassan; Hiroki Iida; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-02-12       Impact factor: 15.419
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  9 in total

1.  Catalytic Nucleophilic Allylation Driven by the Water-Gas Shift Reaction.

Authors:  Scott E Denmark; Zachery D Matesich; Son T Nguyen; Selena Milicevic Sephton
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Review 2.  Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.

Authors:  Rosalie S Doerksen; Cole C Meyer; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-26       Impact factor: 15.336

3.  Total Synthesis of Clavosolide A via Asymmetric Alcohol-Mediated Carbonyl Allylation: Beyond Protecting Groups or Chiral Auxiliaries in Polyketide Construction.

Authors:  James M Cabrera; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-24       Impact factor: 15.336

4.  Total Synthesis and Structural Validation of Phosdiecin A via Asymmetric Alcohol-Mediated Carbonyl Reductive Coupling.

Authors:  Franco Della-Felice; Ariel M Sarotti; Michael J Krische; Ronaldo A Pilli
Journal:  J Am Chem Soc       Date:  2019-08-21       Impact factor: 15.419

5.  Reductive C-C Coupling via Hydrogenation and Transfer Hydrogenation: Departure from Stoichiometric Metals in Carbonyl Addition.

Authors:  James Roane; Michael Holmes; Michael J Krische
Journal:  Curr Opin Green Sustain Chem       Date:  2017-06-09

6.  Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles.

Authors:  Cole C Meyer; Eliezer Ortiz; Michael J Krische
Journal:  Chem Rev       Date:  2020-03-19       Impact factor: 60.622

7.  Toward Generalization of Iterative Small Molecule Synthesis.

Authors:  Jonathan W Lehmann; Daniel J Blair; Martin D Burke
Journal:  Nat Rev Chem       Date:  2018-03-07       Impact factor: 34.035

8.  Structure-Based Stabilization of Non-native Protein-Protein Interactions of Coronavirus Nucleocapsid Proteins in Antiviral Drug Design.

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Journal:  J Med Chem       Date:  2020-03-11       Impact factor: 7.446

9.  From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

Authors:  Catherine Gazolla Santana; Michael J Krische
Journal:  ACS Catal       Date:  2021-04-22       Impact factor: 13.084
  9 in total

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