Literature DB >> 21413694

Total synthesis and biological evaluation of (-)-9-deoxy-englerin A.

Dmitry B Ushakov1, Vaidotas Navickas, Markus Ströbele, Cäcilia Maichle-Mössmer, Florenz Sasse, Martin E Maier.   

Abstract

An effective total synthesis of (-)-9-deoxy-englerin (4), an analogue of the natural guaiane sesquiterpene englerin A (1), has been achieved. The synthesis features a transannular epoxide opening to construct the 5,7-fused ring system followed by transannular ether formation with mercury(II) trifluoroacetate.
© 2011 American Chemical Society

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Year:  2011        PMID： 21413694     DOI： 10.1021/ol200499t

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 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

2.  Formal synthesis of (-)-englerin A and cytotoxicity studies of truncated englerins.

Authors:  Jing Xu; Eduardo J E Caro-Diaz; Ayse Batova; Steven D E Sullivan; Emmanuel A Theodorakis
Journal:  Chem Asian J       Date:  2012-03-13

Review 3.  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

4.  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

5.  Synthesis of the spiroiminal moiety and approaches to the synthesis of marineosins A and B.

Authors:  Xiao-Chuan Cai; Barry B Snider
Journal:  J Org Chem       Date:  2013-11-21       Impact factor: 4.354

6.  A formal synthesis of (-)-englerin A by relay ring closing metathesis and transannular etherification.

Authors:  Jungyong Lee; Kathlyn A Parker
Journal:  Org Lett       Date:  2012-05-07       Impact factor: 6.005

7.  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

8.  Englerin a selectively induces necrosis in human renal cancer cells.

Authors:  Florian J Sulzmaier; Zhenwu Li; Mika L Nakashige; David M Fash; William J Chain; Joe W Ramos
Journal:  PLoS One       Date:  2012-10-22       Impact factor: 3.240

9.  A concise enantioselective synthesis of the guaiane sesquiterpene (-)-oxyphyllol.

Authors:  Martin Zahel; Peter Metz
Journal:  Beilstein J Org Chem       Date:  2013-10-08       Impact factor: 2.883

10.  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
  10 in total

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