Literature DB >> 33609222

Cross-coupling reactions towards the synthesis of natural products.

Shaheera Tabassum1, Ameer Fawad Zahoor2, Sajjad Ahmad3, Razia Noreen4, Samreen Gul Khan1, Hamad Ahmad5.   

Abstract

Cross-coupling reactions are powerful synthetic tools for the formation of remarkable building blocks of many naturally occurring molecules, polymers and biologically active compounds. These reactions have brought potent transformations in chemical and pharmaceutical disciplines. In this review, we have focused on the use of cross-coupling reactions such as Suzuki, Negishi, Heck, Sonogashira and Stille in the total synthesis of some natural products of recent years (2016-2020). A short introduction of mentioned cross-coupling reactions along with highlighted aspects of natural products has been stated in separate sections. Additionally, few examples of natural products via incorporation of more than one type of cross-coupling reaction have also been added to demonstrate the importance of these reactions in organic synthesis.
© 2021. The Author(s), under exclusive licence to Springer Nature Switzerland AG part of Springer Nature.

Entities:  

Keywords:  Alkaloids; Cross-coupling; C–C bond; Natural products; Terpenoids

Mesh:

Substances:

Year:  2021        PMID: 33609222     DOI: 10.1007/s11030-021-10195-6

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  55 in total

1.  Practical Intermolecular Hydroarylation of Terminal Alkenes via Reductive Heck Coupling.

Authors:  John A Gurak; Keary M Engle
Journal:  ACS Catal       Date:  2018-08-24       Impact factor: 13.084

2.  Lynamicin D an antimicrobial natural product affects splicing by inducing the expression of SR protein kinase 1.

Authors:  Ioanna Sigala; George Ganidis; Savvas Thysiadis; Alexandros L Zografos; Thomas Giannakouros; Vasiliki Sarli; Eleni Nikolakaki
Journal:  Bioorg Med Chem       Date:  2017-01-19       Impact factor: 3.641

Review 3.  Synthetic applications and methodology development of Chan-Lam coupling: a review.

Authors:  Iqra Munir; Ameer Fawad Zahoor; Nasir Rasool; Syed Ali Raza Naqvi; Khalid Mahmood Zia; Raheel Ahmad
Journal:  Mol Divers       Date:  2018-08-30       Impact factor: 2.943

4.  Alkylboranes in the Suzuki-Miyaura Coupling: Stereochemical and Mechanistic Studies.

Authors:  Karl Matos; John A. Soderquist
Journal:  J Org Chem       Date:  1998-02-06       Impact factor: 4.354

5.  Suzuki cross-coupling reactions of potassium alkenyltrifluoroborates.

Authors:  Gary A Molander; Marta Rodríguez Rivero
Journal:  Org Lett       Date:  2002-01-10       Impact factor: 6.005

6.  Bimetallic oxidative addition involving radical intermediates in nickel-catalyzed alkyl-alkyl Kumada coupling reactions.

Authors:  Jan Breitenfeld; Jesus Ruiz; Matthew D Wodrich; Xile Hu
Journal:  J Am Chem Soc       Date:  2013-08-01       Impact factor: 15.419

7.  Palladium-catalyzed Hiyama cross-coupling reactions of aryl mesylates.

Authors:  Liang Zhang; Jiang Qing; Pengyuan Yang; Jie Wu
Journal:  Org Lett       Date:  2008-10-11       Impact factor: 6.005

8.  Lynamicins A-E, chlorinated bisindole pyrrole antibiotics from a novel marine actinomycete.

Authors:  Katherine A McArthur; Scott S Mitchell; Ginger Tsueng; Arnold Rheingold; Donald J White; Jennifer Grodberg; Kin S Lam; Barbara C M Potts
Journal:  J Nat Prod       Date:  2008-10-09       Impact factor: 4.050

9.  Design and Preparation of New Palladium Precatalysts for C-C and C-N Cross-Coupling Reactions.

Authors:  Nicholas C Bruno; Matthew T Tudge; Stephen L Buchwald
Journal:  Chem Sci       Date:  2013       Impact factor: 9.825

10.  Synthesis of 1,3-Diynes via Cadiot-Chodkiewicz Coupling of Volatile, in Situ Generated Bromoalkynes.

Authors:  Phil C Knutson; Haleigh E Fredericks; Eric M Ferreira
Journal:  Org Lett       Date:  2018-10-17       Impact factor: 6.005

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  4 in total

1.  Palladium(0)-catalyzed aryne annulation: a powerful strategy for the synthesis of thio-bridged compounds.

Authors:  Mayur I Morja; Kishor H Chikhalia
Journal:  Mol Divers       Date:  2022-04-22       Impact factor: 2.943

2.  In-Situ Bromination Enables Formal Cross-Electrophile Coupling of Alcohols with Aryl and Alkenyl Halides.

Authors:  Benjamin K Chi; Jonas K Widness; Michael M Gilbert; Daniel C Salgueiro; Kevin J Garcia; Daniel J Weix
Journal:  ACS Catal       Date:  2021-12-21       Impact factor: 13.084

Review 3.  Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm.

Authors:  Christopher S Horbaczewskyj; Ian J S Fairlamb
Journal:  Org Process Res Dev       Date:  2022-07-11       Impact factor: 3.858

4.  Automated grindstone chemistry: a simple and facile way for PEG-assisted stoichiometry-controlled halogenation of phenols and anilines using N-halosuccinimides.

Authors:  Dharmendra Das; Akhil A Bhosle; Amrita Chatterjee; Mainak Banerjee
Journal:  Beilstein J Org Chem       Date:  2022-08-09       Impact factor: 2.544

  4 in total

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