Literature DB >> 24500870

Total synthesis of resveratrol-based natural products using a palladium-catalyzed decarboxylative arylation and an oxidative Heck reaction.

Felix Klotter1, Armido Studer.   

Abstract

Controlled access to resveratrol-based natural products is offered by a novel, modular concept. A common building block readily available on a large scale serves as the starting material for the introduction of structurally important aryl groups by a Pd-catalyzed decarboxylative arylation and an oxidative Heck reaction with good yields and high stereoselectivity. The modular approach is convincingly documented by the successful synthesis of three racemic resveratrol-based natural products (quadrangularin A, ampelopsin D, and pallidol).
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  decarboxylative coupling; natural products; palladium; resveratrol; total synthesis

Mesh:

Substances:

Year:  2014        PMID: 24500870     DOI: 10.1002/anie.201310676

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


  10 in total

Review 1.  Chemistry and Biology of Resveratrol-Derived Natural Products.

Authors:  Mitchell H Keylor; Bryan S Matsuura; Corey R J Stephenson
Journal:  Chem Rev       Date:  2015-04-02       Impact factor: 60.622

2.  Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the Resultant Quinone Methide Dimers.

Authors:  Kevin J Romero; Matthew S Galliher; Mark A R Raycroft; Jean-Philippe R Chauvin; Irene Bosque; Derek A Pratt; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-26       Impact factor: 15.336

3.  A scalable biomimetic synthesis of resveratrol dimers and systematic evaluation of their antioxidant activities.

Authors:  Bryan S Matsuura; Mitchell H Keylor; Bo Li; YuXuan Lin; Shelby Allison; Derek A Pratt; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-04       Impact factor: 15.336

Review 4.  Recent strategies and tactics for the enantioselective total syntheses of cyclolignan natural products.

Authors:  Rebekah G Reynolds; Huong Quynh Anh Nguyen; Jordan C T Reddel; Regan J Thomson
Journal:  Nat Prod Rep       Date:  2022-03-23       Impact factor: 13.423

5.  Synthesis of resveratrol tetramers via a stereoconvergent radical equilibrium.

Authors:  Mitchell H Keylor; Bryan S Matsuura; Markus Griesser; Jean-Philippe R Chauvin; Ryan A Harding; Mariia S Kirillova; Xu Zhu; Oliver J Fischer; Derek A Pratt; Corey R J Stephenson
Journal:  Science       Date:  2016-12-09       Impact factor: 47.728

6.  Synthesis of Vitisins A and D Enabled by a Persistent Radical Equilibrium.

Authors:  Kevin J Romero; Mitchell H Keylor; Markus Griesser; Xu Zhu; Ethan J Strobel; Derek A Pratt; Corey R J Stephenson
Journal:  J Am Chem Soc       Date:  2020-03-24       Impact factor: 15.419

7.  Total Synthesis of Viniferifuran, Resveratrol-Piceatannol Hybrid, Anigopreissin A and Analogues - Investigation of Demethylation Strategies.

Authors:  Duc Duy Vo; Mikael Elofsson
Journal:  Adv Synth Catal       Date:  2016-12-08       Impact factor: 5.837

8.  Three-component vicinal-diarylation of alkenes via direct transmetalation of arylboronic acids.

Authors:  Yun Zhang; Gong Chen; Dongbing Zhao
Journal:  Chem Sci       Date:  2019-07-03       Impact factor: 9.825

9.  Synthesis of cis-Oriented Vicinal Diphenylethylenes through a Lewis Acid-Promoted Annulation of Oxotriphenylhexanoates.

Authors:  Martin Kamlar; Elin Henriksson; Ivana Císařová; Marcus Malo; Henrik Sundén
Journal:  J Org Chem       Date:  2021-06-17       Impact factor: 4.354

10.  Oral administration of ampelopsin protects against acute brain injury in rats following focal cerebral ischemia.

Authors:  Xiao-Li Ye; Ling-Qun Lu; Wei Li; Qi Lou; Hong-Gang Guo; Qiao-Juan Shi
Journal:  Exp Ther Med       Date:  2017-03-08       Impact factor: 2.447

  10 in total

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