Literature DB >> 20669919

Enantioselective formal synthesis of (-)-englerin A via a Rh-catalyzed [4 + 3] cycloaddition reaction.

Jing Xu1, Eduardo J E Caro-Diaz, Emmanuel A Theodorakis.   

Abstract

An enantioselective formal synthesis of (-)-englerin A (1) is reported. Key to the strategy is a Rh-catalyzed [4 + 3] cycloaddition reaction between furan 10 and diazo ester 11 that, following an intramolecular aldol condensation, produces the tricyclic scaffold of englerin. This strategy also provides a rapid, efficient, and stereoselective access to the biologically significant core motif of the guaiane sesquiterpenes.

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Year:  2010        PMID： 20669919      PMCID： PMC2927118          DOI： 10.1021/ol1015652

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


  10 in total

1.  Enantioselective synthesis of (-)-englerins A and B.

Authors:  Kian Molawi; Nicolas Delpont; Antonio M Echavarren
Journal:  Angew Chem Int Ed Engl       Date:  2010-05-03       Impact factor: 15.336

2.  Prins cyclizations in Au-catalyzed reactions of enynes.

Authors:  Eloísa Jiménez-Núñez; Christelle K Claverie; Cristina Nieto-Oberhuber; Antonio M Echavarren
Journal:  Angew Chem Int Ed Engl       Date:  2006-08-18       Impact factor: 15.336

3.  Total synthesis and absolute configuration of the guaiane sesquiterpene englerin A.

Authors:  Matthieu Willot; Lea Radtke; Daniel Könning; Roland Fröhlich; Viktoria H Gessner; Carsten Strohmann; Mathias Christmann
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Stereoselective gold-catalyzed cycloaddition of functionalized ketoenynes: synthesis of (+)-orientalol F.

Authors:  Eloísa Jiménez-Núñez; Kian Molawi; Antonio M Echavarren
Journal:  Chem Commun (Camb)       Date:  2009-11-05       Impact factor: 6.222

5.  A total synthesis of norhalichondrin B.

Authors:  Katrina L Jackson; James A Henderson; Hajime Motoyoshi; Andrew J Phillips
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Guaiane-type sesquiterpenoids from Alisma orientalis.

Authors:  Guo-Ping Peng; Gang Tian; Xian-Feng Huang; Feng-Chang Lou
Journal:  Phytochemistry       Date:  2003-08       Impact factor: 4.072

7.  Cancer statistics, 2009.

Authors:  Ahmedin Jemal; Rebecca Siegel; Elizabeth Ward; Yongping Hao; Jiaquan Xu; Michael J Thun
Journal:  CA Cancer J Clin       Date:  2009-05-27       Impact factor: 508.702

8.  Englerin A, a selective inhibitor of renal cancer cell growth, from Phyllanthus engleri.

Authors:  Ranjala Ratnayake; David Covell; Tanya T Ransom; Kirk R Gustafson; John A Beutler
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

9.  Total synthesis of englerin A.

Authors:  K C Nicolaou; Qiang Kang; Sin Yee Ng; David Y-K Chen
Journal:  J Am Chem Soc       Date:  2010-06-16       Impact factor: 15.419

10.  Determination of absolute structure using Bayesian statistics on Bijvoet differences.

Authors:  Rob W W Hooft; Leo H Straver; Anthony L Spek
Journal:  J Appl Crystallogr       Date:  2008-01-16       Impact factor: 3.304
  10 in total
  14 in total

1.  Reversal of the regiochemistry in the rhodium-catalyzed [4+3] cycloaddition between vinyldiazoacetates and dienes.

Authors:  Pablo E Guzmán; Yajing Lian; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-29       Impact factor: 15.336

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

4.  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

5.  Enantioselective synthesis of 2,2,5-tri- and 2,2,5,5-tetrasubstituted tetrahydrofurans via [4 + 2] cycloaddition and ring-opening cross-metathesis.

Authors:  Noah M Benjamin; Stephen F Martin
Journal:  Org Lett       Date:  2011-01-06       Impact factor: 6.005

Review 6.  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

Review 7.  Cycloaddition reactions of enoldiazo compounds.

Authors:  Qing-Qing Cheng; Yongming Deng; Marianne Lankelma; Michael P Doyle
Journal:  Chem Soc Rev       Date:  2017-08-29       Impact factor: 54.564

Review 8.  A continuum of progress: applications of N-hetereocyclic carbene catalysis in total synthesis.

Authors:  Javier Izquierdo; Gerri E Hutson; Daniel T Cohen; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-16       Impact factor: 15.336

9.  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

10.  (-)-Englerin A is a potent and selective activator of TRPC4 and TRPC5 calcium channels.

Authors:  Yasemin Akbulut; Hannah J Gaunt; Katsuhiko Muraki; Melanie J Ludlow; Mohamed S Amer; Alexander Bruns; Naveen S Vasudev; Lea Radtke; Matthieu Willot; Sven Hahn; Tobias Seitz; Slava Ziegler; Mathias Christmann; David J Beech; Herbert Waldmann
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-23       Impact factor: 15.336
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