Literature DB >> 22871030

Stereocontrolled total synthesis of (-)-englerin A.

Keisuke Takahashi1, Keita Komine, Yuichi Yokoi, Jun Ishihara, Susumi Hatakeyama.   

Abstract

The total synthesis of (-)-englerin A, a potent and selective inhibitor of renal cancer cell lines, is described. The key feature includes the stereocontrolled construction of the cyclopentane structure by taking advantage of a base-promoted epoxynitrile cyclization.

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Year:  2012        PMID： 22871030     DOI： 10.1021/jo301145r

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  9 in total

1.  Reassignment of the absolute configuration of plakinidone from the sponge consortium Plakortis halichondrioides-Xestospongia deweerdtae using a combination of synthesis and a chiroptical approach.

Authors:  Carlos Jiménez-Romero; Joanna E Rode; Abimael D Rodríguez
Journal:  Tetrahedron Asymmetry       Date:  2016-04-07

Review 2.  Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.

Authors:  Zachary G Brill; Matthew L Condakes; Chi P Ting; Thomas J Maimone
Journal:  Chem Rev       Date:  2017-03-15       Impact factor: 60.622

3.  Synthesis of a stable and orally bioavailable englerin analogue.

Authors:  David M Fash; Cody J Peer; Zhenwu Li; Ian J Talisman; Sima Hayavi; Florian J Sulzmaier; Joe W Ramos; Carole Sourbier; Leonard Neckers; W Douglas Figg; John A Beutler; William J Chain
Journal:  Bioorg Med Chem Lett       Date:  2016-04-08       Impact factor: 2.823

Review 4.  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

5.  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

6.  Formal synthesis of englerin A utilizing regio- and diastereoselective [4+3] cycloaddition.

Authors:  Shuichi Hagihara; Kengo Hanaya; Takeshi Sugai; Mitsuru Shoji
Journal:  J Antibiot (Tokyo)       Date:  2017-08-02       Impact factor: 2.649

7.  Chemoselective formal β-functionalization of substituted aliphatic amides enabled by a facile stereoselective oxidation event.

Authors:  Adriano Bauer; Nuno Maulide
Journal:  Chem Sci       Date:  2019-09-10       Impact factor: 9.825

8.  Concise asymmetric synthesis of two natural oxacyclododecindione-type macrolactones from industrial waste.

Authors:  Xian Liu; Huifang Nie; Lin Yao; Ru Jiang; Weiping Chen
Journal:  RSC Adv       Date:  2020-04-30       Impact factor: 3.361

9.  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
  9 in total

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