Literature DB >> 22235754

Rapid access to conformational analogues of (+)-peloruside A.

Zhiming Zhao1, Richard E Taylor.   

Abstract

An efficient synthetic strategy for rapid access to analogues of peloruside A has been demonstrated. The synthetic route was highlighted by a simple esterification-based fragment coupling and a late stage ring-closing metathesis reaction. This convergent route has provided access to rationally designed analogues inspired by the solution conformational preferences of peloruside A.
© 2012 American Chemical Society

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Year:  2012        PMID: 22235754      PMCID: PMC3272296          DOI: 10.1021/ol203268t

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


  17 in total

1.  Structure-activity studies of the pelorusides: new congeners and semi-synthetic analogues.

Authors:  A Jonathan Singh; Mina Razzak; Paul Teesdale-Spittle; Thomas N Gaitanos; Anja Wilmes; Ian Paterson; Jonathan M Goodman; John H Miller; Peter T Northcote
Journal:  Org Biomol Chem       Date:  2011-04-21       Impact factor: 3.876

2.  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

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.  Peloruside A does not bind to the taxoid site on beta-tubulin and retains its activity in multidrug-resistant cell lines.

Authors:  Thomas N Gaitanos; Rubén M Buey; J Fernando Díaz; Peter T Northcote; Paul Teesdale-Spittle; José M Andreu; John H Miller
Journal:  Cancer Res       Date:  2004-08-01       Impact factor: 12.701

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

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

6.  Peloruside A enhances apoptosis in H-ras-transformed cells and is cytotoxic to proliferating T cells.

Authors:  J H Miller; B Rouwé; T N Gaitanos; K A Hood; K P Crume; B T Bäckström; A C La Flamme; M V Berridge; P T Northcote
Journal:  Apoptosis       Date:  2004-11       Impact factor: 4.677

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

Review 8.  Strategies for the synthesis of the novel antitumor agent peloruside A.

Authors:  David R Williams; Partha P Nag; Nicolas Zorn
Journal:  Curr Opin Drug Discov Devel       Date:  2008-03

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.  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

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  4 in total

Review 1.  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 2.  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

3.  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

4.  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

  4 in total

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