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Literature DB >> 21390391

Recent developments in natural product synthesis using metal-catalysed C-H bond functionalisation.

Lindsay McMurray¹, Fionn O'Hara, Matthew J Gaunt.

Abstract

Metal-catalysed C-H bond functionalisation has had a significant impact on how chemists make molecules. Translating the methodological developments to their use in the assembly of complex natural products is an important challenge for the continued advancement of chemical synthesis. In this tutorial review, we describe selected recent examples of how the metal-catalysed C-H bond functionalisation has been able to positively affect the synthesis of natural products.

Entities: Chemical

Mesh：

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Year: 2011 PMID： 21390391 DOI： 10.1039/c1cs15013h

Source DB: PubMed Journal: Chem Soc Rev ISSN： 0306-0012 Impact factor: 54.564

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Cited

125 in total

1. Total synthesis and structural revision of the piperarborenines via sequential cyclobutane C-H arylation.

Authors: Will R Gutekunst; Phil S Baran
Journal: J Am Chem Soc Date: 2011-11-08 Impact factor: 15.419

2. Combined C-H functionalization/Cope rearrangement with vinyl ethers as a surrogate for the vinylogous Mukaiyama aldol reaction.

Authors: Yajing Lian; Huw M L Davies
Journal: J Am Chem Soc Date: 2011-07-18 Impact factor: 15.419

3. C-H bond activation enables the rapid construction and late-stage diversification of functional molecules.

Authors: Joanna Wencel-Delord; Frank Glorius
Journal: Nat Chem Date: 2013-05 Impact factor: 24.427

4. C-H Activation: A surrogate for selectivity.

Authors: Eric M Ferreira
Journal: Nat Chem Date: 2014-02 Impact factor: 24.427

Review 5. Enzymatic CH functionalizations for natural product synthesis.

Authors: Fuzhuo Li; Xiao Zhang; Hans Renata
Journal: Curr Opin Chem Biol Date: 2018-09-27 Impact factor: 8.822

6. Iridium-Catalyzed Silylation of C-H Bonds in Unactivated Arenes: A Sterically Encumbered Phenanthroline Ligand Accelerates Catalysis.

Authors: Caleb Karmel; Zhewei Chen; John F Hartwig
Journal: J Am Chem Soc Date: 2019-04-23 Impact factor: 15.419

Recent developments in natural product synthesis using metal-catalysed C-H bond functionalisation.

1. Total synthesis and structural revision of the piperarborenines via sequential cyclobutane C-H arylation.

2. Combined C-H functionalization/Cope rearrangement with vinyl ethers as a surrogate for the vinylogous Mukaiyama aldol reaction.

3. C-H bond activation enables the rapid construction and late-stage diversification of functional molecules.

4. C-H Activation: A surrogate for selectivity.

Review 5. Enzymatic CH functionalizations for natural product synthesis.

6. Iridium-Catalyzed Silylation of C-H Bonds in Unactivated Arenes: A Sterically Encumbered Phenanthroline Ligand Accelerates Catalysis.

7. Meta-selective C-H functionalization using a nitrile-based directing group and cleavable Si-tether.

8. Synthesis of isoquinuclidines from highly substituted dihydropyridines via the Diels-Alder reaction.

9. Pd(II)-catalyzed C-H functionalizations directed by distal weakly coordinating functional groups.

10. Scope and limitations of auxiliary-assisted, palladium-catalyzed arylation and alkylation of sp2 and sp3 C-H bonds.