Literature DB >> 19249829

An aldol-based synthesis of (+)-peloruside a, a potent microtubule stabilizing agent.

David A Evans1, Dennie S Welch, Alexander W H Speed, George A Moniz, Andreas Reichelt, Stephen Ho.   

Abstract

A convergent synthesis of the marine natural product (+)-peloruside has been reported. This target has been assembled through the successive application of two methyl ketone boron aldol addition reactions to the latent C(7)-C(11) dialdehyde synthon. This approach afforded a 22-step synthesis of this natural product. The influence of resident stereocenters on aldol reaction diastereoselection has been examined in detail.

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Year:  2009        PMID： 19249829      PMCID： PMC3357919          DOI： 10.1021/ja900020a

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  10 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.  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

3.  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

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

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

5.  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

6.  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

7.  Asymmetric induction in methyl ketone aldol additions to alpha-alkoxy and alpha,beta-bisalkoxy aldehydes: a model for acyclic stereocontrol.

Authors:  David A Evans; Victor J Cee; Sarah J Siska
Journal:  J Am Chem Soc       Date:  2006-07-26       Impact factor: 15.419

8.  Enantioselective total synthesis of peloruside A: a potent microtubule stabilizer.

Authors:  Arun K Ghosh; Xiaoming Xu; Jae-Hun Kim; Chun-Xiao Xu
Journal:  Org Lett       Date:  2008-02-05       Impact factor: 6.005

9.  1,5-asymmetric induction in boron-mediated beta-alkoxy methyl ketone aldol addition reactions.

Authors:  David A Evans; Bernard Côté; Paul J Coleman; Brian T Connell
Journal:  J Am Chem Soc       Date:  2003-09-10       Impact factor: 15.419

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
  10 in total
  14 in total

1.  Toward the synthesis of (+)-peloruside A via an intramolecular vinylogous aldol reaction.

Authors:  Jeffrey A Gazaille; Joseph A Abramite; Tarek Sammakia
Journal:  Org Lett       Date:  2011-12-12       Impact factor: 6.005

2.  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

3.  Super silyl stereo-directing groups for complete 1,5-syn and -anti stereoselectivities in the aldol reactions of beta-siloxy methyl ketones with aldehydes.

Authors:  Yousuke Yamaoka; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2010-04-21       Impact factor: 15.419

Review 4.  Conformation-activity relationships of polyketide natural products.

Authors:  Erik M Larsen; Matthew R Wilson; Richard E Taylor
Journal:  Nat Prod Rep       Date:  2015-08       Impact factor: 13.423

Review 5.  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

6.  An enantioselective total synthesis of (+)-peloruside A.

Authors:  Meredeth A McGowan; Christian P Stevenson; Matthew A Schiffler; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-16       Impact factor: 15.336

7.  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

Review 8.  Microtubule-stabilizing drugs from marine sponges: focus on peloruside A and zampanolide.

Authors:  John H Miller; A Jonathan Singh; Peter T Northcote
Journal:  Mar Drugs       Date:  2010-03-31       Impact factor: 5.118

9.  Highly convergent synthesis of peluroside A.

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

10.  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
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