Literature DB >> 15787492

Total synthesis of (+)-peloruside A.

Meizhong Jin1, Richard E Taylor.   

Abstract

[reaction: see text] A total synthesis of (+)-peloruside A has been successfully achieved. The strategy was highlighted by a late stage aldol coupling of two complex fragments followed by an intramolecular hemi-ketal cyclization, a MOM group participated epoxide ring fragmentation reaction, and a highly selective methylation. This convergent route allows access to rationally designed analogues.

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Year:  2005        PMID: 15787492     DOI: 10.1021/ol050070g

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


  22 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 laulimalide: synthesis of the northern and southern fragments.

Authors:  Barry M Trost; W Michael Seganish; Cheol K Chung; Dominique Amans
Journal:  Chemistry       Date:  2012-02-03       Impact factor: 5.236

3.  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

4.  Electrophile-induced ether transfer: a new approach to polyketide structural units.

Authors:  Kai Liu; Richard E Taylor; Rendy Kartika
Journal:  Org Lett       Date:  2006-11-09       Impact factor: 6.005

Review 5.  Sponge-associated microorganisms: evolution, ecology, and biotechnological potential.

Authors:  Michael W Taylor; Regina Radax; Doris Steger; Michael Wagner
Journal:  Microbiol Mol Biol Rev       Date:  2007-06       Impact factor: 11.056

Review 6.  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 7.  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

8.  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 9.  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

Review 10.  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

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