Literature DB >> 12583779

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

Ian Paterson1, M Emilia Di Francesco, Toralf Kühn.   

Abstract

[reaction: see text] The asymmetric synthesis of building blocks 3, 4, and 5, corresponding to C(12)-C(19), C(7)-C(11), and C(1)-C(6) segments of peloruside A, is reported, along with boron-mediated aldol coupling studies directed toward the assembly of the complete carbon skeleton of this microtubule-stabilizing macrolide.

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Year:  2003        PMID： 12583779     DOI： 10.1021/ol034035q

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


  14 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

2.  An enantioselective synthesis of the C1-C9 segment of antitumor macrolide peloruside A.

Authors:  Arun K Ghosh; Jae-Hun Kim
Journal:  Tetrahedron Lett       Date:  2003-04-24       Impact factor: 2.415

3.  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

4.  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

5.  Synthetic studies of microtubule stabilizing agent peloruside A: an asymmetric synthesis of C10-C24 segment.

Authors:  Arun K Ghosh; Jae-Hun Kim
Journal:  Tetrahedron Lett       Date:  2003-09-13       Impact factor: 2.415

6.  Synthesis of the entire framework of tartrolon B utilizing a silicon-tethered ring-closing metathesis strategy.

Authors:  Yi Jin Kim; Daesung Lee
Journal:  Org Lett       Date:  2006-11-09       Impact factor: 6.005

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.  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

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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