Literature DB >> 35089624

Synthesis of Natural Products by C-H Functionalization of Heterocycless.

Yang Zhang1, Michal Szostak1.   

Abstract

Total synthesis is considered by many as the finest combination of art and science. During the last decades, several concepts were proposed for achieving the perfect vision of total synthesis, such as atom economy, step economy, or redox economy. In this context, C-H functionalization represents the most powerful platform that has emerged in the last years, empowering rapid synthesis of complex natural products and enabling diversification of bioactive scaffolds based on natural product architectures. In this review, we present an overview of the recent strategies towards the total synthesis of heterocyclic natural products enabled by C-H functionalization. Heterocycles represent the most common motifs in drug discovery and marketed drugs. The implementation of C-H functionalization of heterocycles enables novel tactics in the construction of core architectures, but also changes the logic design of retrosynthetic strategies and permits access to natural product scaffolds with novel and enhanced biological activities.
© 2022 Wiley-VCH GmbH.

Entities:  

Keywords:  C−H activation; C−H functionalization; heterocycles; natural products; total synthesis

Mesh:

Substances:

Year:  2022        PMID: 35089624      PMCID: PMC9035081          DOI: 10.1002/chem.202104278

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.020


  70 in total

1.  Weak coordination as a powerful means for developing broadly useful C-H functionalization reactions.

Authors:  Keary M Engle; Tian-Sheng Mei; Masayuki Wasa; Jin-Quan Yu
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2.  Redox economy in organic synthesis.

Authors:  Noah Z Burns; Phil S Baran; Reinhard W Hoffmann
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  Total Synthesis of the Caged Indole Alkaloid Arboridinine Enabled by aza-Prins and Metal-Mediated Cyclizations.

Authors:  Pei Gan; Jennifer Pitzen; Pei Qu; Scott A Snyder
Journal:  J Am Chem Soc       Date:  2018-01-08       Impact factor: 15.419

4.  C-H functionalization in organic synthesis.

Authors:  Huw M L Davies; Justin Du Bois; Jin-Quan Yu
Journal:  Chem Soc Rev       Date:  2011-03-10       Impact factor: 54.564

5.  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

6.  Collective Total Synthesis of (-)-Lundurines A-C.

Authors:  Wei Xu; Jianfei Zhao; Cheng Tao; Huifei Wang; Yun Li; Bin Cheng; Hongbin Zhai
Journal:  Org Lett       Date:  2018-03-08       Impact factor: 6.005

7.  Formal Total Syntheses of (-)- and (+)-Actinophyllic Acid.

Authors:  Fei Xue; Huifang Lu; Liping He; Wenfei Li; Dan Zhang; Xiao-Yu Liu; Yong Qin
Journal:  J Org Chem       Date:  2018-01-10       Impact factor: 4.354

8.  Improved Total Synthesis of Tubulysins and Design, Synthesis, and Biological Evaluation of New Tubulysins with Highly Potent Cytotoxicities against Cancer Cells as Potential Payloads for Antibody-Drug Conjugates.

Authors:  K C Nicolaou; Rohan D Erande; Jun Yin; Dionisios Vourloumis; Monette Aujay; Joseph Sandoval; Stefan Munneke; Julia Gavrilyuk
Journal:  J Am Chem Soc       Date:  2018-01-30       Impact factor: 15.419

9.  A Concise Enantioselective Total Synthesis of (-)-Deoxoapodine.

Authors:  Kei Yoshida; Kosuke Okada; Hirofumi Ueda; Hidetoshi Tokuyama
Journal:  Angew Chem Int Ed Engl       Date:  2020-10-15       Impact factor: 15.336

Review 10.  Natural products in drug discovery: advances and opportunities.

Authors:  Atanas G Atanasov; Sergey B Zotchev; Verena M Dirsch; Claudiu T Supuran
Journal:  Nat Rev Drug Discov       Date:  2021-01-28       Impact factor: 112.288

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