Literature DB >> 19007239

Total synthesis of (-)-2-epi-peloruside A.

Amos B Smith1, Jason M Cox, Noriyuki Furuichi, Craig S Kenesky, Junying Zheng, Onur Atasoylu, William M Wuest.   

Abstract

A convergent synthesis of (-)-2-epi-peloruside A has been achieved. Highlights include implementation of multicomponent type I anion relay chemistry (ARC) to unite 2-TBS-1,3-dithiane with two epoxides to construct the eastern hemisphere, a late-stage dithiane union to secure the complete, fully functionalized carbon backbone, and Yamaguchi macrolactonization, which led to (-)-2-epi-peloruside A via an unexpected epimerization at C(2).

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Year:  2008        PMID： 19007239      PMCID： PMC2697658          DOI： 10.1021/ol8019132

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


  18 in total

1.  Toward a total synthesis of peloruside A: enantioselective preparation of the C8-C19 region.

Authors:  Richard E Taylor; Meizhong Jin
Journal:  Org Lett       Date:  2003-12-25       Impact factor: 6.005

2.  Toward the total synthesis of natural peloruside a: stereoselective synthesis of the backbone of the core.

Authors:  Bo Liu; Wei-Shan Zhou
Journal:  Org Lett       Date:  2004-01-08       Impact factor: 6.005

3.  Total synthesis and absolute configuration of the novel microtubule-stabilizing agent peloruside A.

Authors:  Xibin Liao; Yusheng Wu; Jef K De Brabander
Journal:  Angew Chem Int Ed Engl       Date:  2003-04-11       Impact factor: 15.336

4.  Stereoselective synthesis of the C(1)-C(11) fragment of peloruside A.

Authors:  Robert M Owen; William R Roush
Journal:  Org Lett       Date:  2005-09-01       Impact factor: 6.005

5.  Total synthesis of (+)-peloruside A.

Authors:  Meizhong Jin; Richard E Taylor
Journal:  Org Lett       Date:  2005-03-31       Impact factor: 6.005

6.  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

7.  Peloruside A: a potent cytotoxic macrolide isolated from the new zealand marine sponge Mycale sp.

Authors:  L M West; P T Northcote; C N Battershill
Journal:  J Org Chem       Date:  2000-01-28       Impact factor: 4.354

8.  Toward the synthesis of peloruside a: fragment synthesis and coupling studies.

Authors:  Ian Paterson; M Emilia Di Francesco; Toralf Kühn
Journal:  Org Lett       Date:  2003-02-20       Impact factor: 6.005

9.  A unique mode of microtubule stabilization induced by peloruside A.

Authors:  J Torin Huzil; John K Chik; Gordon W Slysz; Holly Freedman; Jack Tuszynski; Richard E Taylor; Dan L Sackett; David C Schriemer
Journal:  J Mol Biol       Date:  2008-03-19       Impact factor: 5.469

10.  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
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  8 in total

1.  Total synthesis of peloruside A through kinetic lactonization and relay ring-closing metathesis cyclization reactions.

Authors:  Thomas R Hoye; Junha Jeon; Lucas C Kopel; Troy D Ryba; Manomi A Tennakoon; Yini Wang
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-16       Impact factor: 15.336

Review 2.  Microtubule stabilizing agents as potential treatment for Alzheimer's disease and related neurodegenerative tauopathies.

Authors:  Carlo Ballatore; Kurt R Brunden; Donna M Huryn; John Q Trojanowski; Virginia M-Y Lee; Amos B Smith
Journal:  J Med Chem       Date:  2012-09-28       Impact factor: 7.446

3.  Design, synthesis, and biological evaluation of diminutive forms of (+)-spongistatin 1: lessons learned.

Authors:  Amos B Smith; Christina A Risatti; Onur Atasoylu; Clay S Bennett; Junke Liu; Hongsheng Cheng; Karen TenDyke; Qunli Xu
Journal:  J Am Chem Soc       Date:  2011-08-12       Impact factor: 15.419

4.  Reversed-Polarity Synthesis of Diaryl Ketones through Palladium-Catalyzed Direct Arylation of 2-Aryl-1,3-dithianes.

Authors:  Baris Yucel; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2014-11-24       Impact factor: 5.837

5.  Peloruside B, a potent antitumor macrolide from the New Zealand marine sponge Mycale hentscheli: isolation, structure, total synthesis, and bioactivity.

Authors:  A Jonathan Singh; Chun-Xiao Xu; Xiaoming Xu; Lyndon M West; Anja Wilmes; Ariane Chan; Ernest Hamel; John H Miller; Peter T Northcote; Arun K Ghosh
Journal:  J Org Chem       Date:  2010-01-01       Impact factor: 4.354

6.  Improved method for the synthesis of beta-carbonyl silyl-1,3-dithianes by the double conjugate addition of 1,3-dithiol to propargylic carbonyl compounds.

Authors:  Sumit Mukherjee; Dimitra Kontokosta; Aditi Patil; Sivakumar Rallapalli; Daesung Lee
Journal:  J Org Chem       Date:  2009-12-04       Impact factor: 4.354

7.  Highly convergent synthesis of peluroside A.

Authors:  Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  Total synthesis of (-)-18-epi-peloruside A: an alkyne linchpin strategy.

Authors:  Barry M Trost; David J Michaelis; Sushant Malhotra
Journal:  Org Lett       Date:  2013-10-04       Impact factor: 6.005
  8 in total

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