Literature DB >> 14682739

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

Richard E Taylor1, Meizhong Jin.   

Abstract

An efficient synthetic sequence toward the C8-C19 region of peloruside A has been developed. The route is highlighted by a selective electrophilic cyclization reaction, a single-step epoxide ring-opening/methylation sequence, and a stereoselective Mukaiyama aldol reaction. [reaction: see text]

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Year:  2003        PMID： 14682739     DOI： 10.1021/ol0358814

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


  16 in total

1.  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

2.  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 3.  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

4.  Expedient synthesis of α,α-dimethyl-β-hydroxy carbonyl scaffolds via Evans' aldol reaction with a tertiary enolate.

Authors:  Joshawna K Nunnery; Takashi L Suyama; Roger G Linington; William H Gerwick
Journal:  Tetrahedron Lett       Date:  2011-06-08       Impact factor: 2.415

5.  C6-C8 bridged epothilones: consequences of installing a conformational lock at the edge of the macrocycle.

Authors:  Weiqiang Zhan; Yi Jiang; Shubhada Sharma; Peggy J Brodie; Susan Bane; David G I Kingston; Dennis C Liotta; James P Snyder
Journal:  Chemistry       Date:  2011-11-30       Impact factor: 5.236

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.  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.  Long-range anion relay chemistry (LR-ARC): a validated ARC tactic.

Authors:  Luis Sanchez; Amos B Smith
Journal:  Org Lett       Date:  2012-12-06       Impact factor: 6.005

10.  Highly convergent synthesis of peluroside A.

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