Literature DB >> 21749032

Enantioselective total synthesis of (-)-zampanolide, a potent microtubule-stabilizing agent.

Arun K Ghosh1, Xu Cheng.   

Abstract

An enantioselective total synthesis of zampanolide has been accomplished using a novel DDQ/Brønsted acid promoted cyclization as the key reaction. The synthesis features cross-metathesis to construct the trisubstituted olefin and a ring-closing metathesis to form the macrolactone. The final N-acyl aminal formation was stereoselectively accomplished by an organocatalytic reaction.
© 2011 American Chemical Society

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Year:  2011        PMID： 21749032      PMCID： PMC3153378          DOI： 10.1021/ol201626h

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


  24 in total

1.  Total synthesis of (+)-zampanolide.

Authors:  A B Smith; I G Safonov; R M Corbett
Journal:  J Am Chem Soc       Date:  2001-12-12       Impact factor: 15.419

2.  Synthesis of (-)-dactylolide and 13-desmethylene-(-)-dactylolide and their effects on tubulin.

Authors:  Didier Zurwerra; Jürg Gertsch; Karl-Heinz Altmann
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

3.  A powerful Brønsted acid catalyst for the organocatalytic asymmetric transfer hydrogenation of imines.

Authors:  Sebastian Hoffmann; Abdul Majeed Seayad; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2005-12-01       Impact factor: 15.336

4.  Total synthesis of (+)-dactylolide through an efficient sequential Peterson olefination and Prins cyclization reaction.

Authors:  Danielle L Aubele; Shuangyi Wan; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2005-05-30       Impact factor: 15.336

5.  Synergistic effects of peloruside A and laulimalide with taxoid site drugs, but not with each other, on tubulin assembly.

Authors:  Ernest Hamel; Billy W Day; John H Miller; M Katherine Jung; Peter T Northcote; Arun K Ghosh; Dennis P Curran; Mark Cushman; K C Nicolaou; Ian Paterson; Erik J Sorensen
Journal:  Mol Pharmacol       Date:  2006-08-03       Impact factor: 4.436

6.  Total synthesis of (+)-dactylolide.

Authors:  Carina C Sanchez; Gary E Keck
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

7.  An efficient, second-generation synthesis of the signature dioxabicyclo[3.2.1]octane core of (+)-sorangicin A and elaboration of the (Z,Z,E)-triene acid system.

Authors:  Amos B Smith; Shuzhi Dong
Journal:  Org Lett       Date:  2009-03-05       Impact factor: 6.005

8.  Laulimalide and paclitaxel: a comparison of their effects on tubulin assembly and their synergistic action when present simultaneously.

Authors:  Eric J Gapud; Ruoli Bai; Arun K Ghosh; Ernest Hamel
Journal:  Mol Pharmacol       Date:  2004-07       Impact factor: 4.436

9.  Peloruside A, a novel antimitotic agent with paclitaxel-like microtubule- stabilizing activity.

Authors:  Kylie A Hood; Lyndon M West; Berber Rouwé; Peter T Northcote; Michael V Berridge; St John Wakefield; John H Miller
Journal:  Cancer Res       Date:  2002-06-15       Impact factor: 12.701

10.  Macrolactonization via Ti(IV)-mediated epoxy-acid coupling: a total synthesis of (-)-dactylolide [and zampanolide].

Authors:  Thomas R Hoye; Min Hu
Journal:  J Am Chem Soc       Date:  2003-08-13       Impact factor: 15.419
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  24 in total

1.  Synthesis of Functionalized 4-Methylenetetrahydropyrans by Oxidative Activation of Cinnamyl or Benzyl Ethers.

Authors:  Arun K Ghosh; Xu Cheng
Journal:  Tetrahedron Lett       Date:  2012-05-16       Impact factor: 2.415

2.  Toward an enantioselective synthesis of (-)-zampanolide: preparation of the C9-C20 region.

Authors:  Matthew R Wilson; Richard E Taylor
Journal:  Org Lett       Date:  2012-06-21       Impact factor: 6.005

3.  Toward the Ideal Synthesis and Transformative Therapies: The Roles of Step Economy and Function Oriented Synthesis.

Authors:  Paul A Wender
Journal:  Tetrahedron       Date:  2013-06-07       Impact factor: 2.457

4.  Synthesis of sulfur-containing heterocycles through oxidative carbon-hydrogen bond functionalization.

Authors:  Yubo Cui; Paul E Floreancig
Journal:  Org Lett       Date:  2012-03-15       Impact factor: 6.005

5.  Synthesis and antiproliferative evaluation of new zampanolide mimics.

Authors:  Guanglin Chen; Manee Patanapongpibul; Ziran Jiang; Qiang Zhang; Shilong Zheng; Guangdi Wang; James D White; Qiao-Hong Chen
Journal:  Org Biomol Chem       Date:  2019-04-10       Impact factor: 3.876

6.  Lead Diversification through a Prins-Driven Macrocyclization Strategy: Application to C13-Diversified Bryostatin Analogues.

Authors:  Paul A Wender; Kelvin L Billingsley
Journal:  Synthesis (Stuttg)       Date:  2013       Impact factor: 3.157

7.  Synthesis, conformational preferences, and biological activity of conformational analogues of the microtubule-stabilizing agents, (-)-zampanolide and (-)-dactylolide.

Authors:  Jeffrey L Henry; Matthew R Wilson; Michael P Mulligan; Taylor R Quinn; Dan L Sackett; Richard E Taylor
Journal:  Medchemcomm       Date:  2019-04-09       Impact factor: 3.597

Review 8.  Recent progress with microtubule stabilizers: new compounds, binding modes and cellular activities.

Authors:  Cristina C Rohena; Susan L Mooberry
Journal:  Nat Prod Rep       Date:  2014-03       Impact factor: 13.423

9.  Total Synthesis of Potent Antitumor Macrolide, (-)-Zampanolide: An Oxidative Intramolecular Cyclization-Based Strategy.

Authors:  Arun K Ghosh; Xu Cheng; Ruoli Bai; Ernest Hamel
Journal:  European J Org Chem       Date:  2012-07-01

10.  Conformational preferences of zampanolide and dactylolide.

Authors:  Erik M Larsen; Matthew R Wilson; Jaroslav Zajicek; Richard E Taylor
Journal:  Org Lett       Date:  2013-10-08       Impact factor: 6.005
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