Literature DB >> 24911263

Total synthesis of (+/-)-4-demethylenglerin A.

Liang Dong1, Xiao-Zhen Jiao, Xiao-Yu Liu, Cheng-Sen Tian, Xiao-Yu Li, Yang-Yang Yao, Ping Xie.   

Abstract

Racemic 4-demethylenglerin A (1'), a simplified analog of the guaiane-type sesquiterpene englerin A (1), has been synthesized. The cyclic hydrocarbon core structure was built through modified Metz approach using epoxynitrile cyclization and direct Aldol reaction to prepare the precursor of RCM. The primary cytotoxicity test summarized that C4 methyl has marked impacts on the bioactivity.

Entities:  

Keywords:  4-demethylenglerin A; epoxynitrile cyclization; total synthesis

Mesh:

Substances:

Year:  2014        PMID: 24911263     DOI: 10.1080/10286020.2014.918111

Source DB:  PubMed          Journal:  J Asian Nat Prod Res        ISSN: 1028-6020            Impact factor:   1.569


  5 in total

1.  Importance of a 4-Alkyl Substituent for Activity in the Englerin Series.

Authors:  Daniel C Elliott; John A Beutler; Kathlyn A Parker
Journal:  ACS Med Chem Lett       Date:  2017-06-06       Impact factor: 4.345

Review 2.  Englerins: A Comprehensive Review.

Authors:  Zhenhua Wu; Senzhi Zhao; David M Fash; Zhenwu Li; William J Chain; John A Beutler
Journal:  J Nat Prod       Date:  2017-02-07       Impact factor: 4.050

3.  Biological Effects of Modifications of the Englerin A Glycolate.

Authors:  Sarath P D Seenadera; Sarah A Long; Rhone Akee; Gabriela Bermudez; Gregory Parsonage; Jonathan Strope; Cody Peer; W Douglas Figg; Kathlyn A Parker; David J Beech; John A Beutler
Journal:  ACS Med Chem Lett       Date:  2022-08-22       Impact factor: 4.632

4.  Bridgehead Modifications of Englerin A Reduce TRPC4 Activity and Intravenous Toxicity but not Cell Growth Inhibition.

Authors:  Zhenhua Wu; Jean-Simon Suppo; Sarka Tumova; Jonathan Strope; Fernando Bravo; Melody Moy; Ethan S Weinstein; Cody J Peer; William D Figg; William J Chain; Antonio M Echavarren; David J Beech; John A Beutler
Journal:  ACS Med Chem Lett       Date:  2020-08-03       Impact factor: 4.345

5.  Synthesis and Biological Evaluation of New (-)-Englerin Analogues.

Authors:  Laura López-Suárez; Lorena Riesgo; Fernando Bravo; Tanya T Ransom; John A Beutler; Antonio M Echavarren
Journal:  ChemMedChem       Date:  2016-03-23       Impact factor: 3.466

  5 in total

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