Literature DB >> 16119937

Stereoselective synthesis of the C(1)-C(11) fragment of peloruside A.

Robert M Owen1, William R Roush.   

Abstract

A highly stereoselective synthesis of the C(1)-C(11) fragment 4 of peloruside A has been accomplished via a stereoselective double allylboration and an intramolecular epoxide opening to provide the functionally dense C(3)-C(11) segment 14. A glycolate aldol reaction was then employed to introduce the remaining stereocenters at C(2)-C(3). [reaction: see text]

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Year:  2005        PMID： 16119937     DOI： 10.1021/ol0514303

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


  12 in total

1.  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

2.  Enantio- and diastereoselective synthesis of (E)-1,5-syn-diols: application to the synthesis of the C(23)-C(40) fragment of tetrafibricin.

Authors:  Jeremy Kister; Philippe Nuhant; Ricardo Lira; Achim Sorg; William R Roush
Journal:  Org Lett       Date:  2011-03-04       Impact factor: 6.005

3.  Development of a Double Allylboration Reagent Targeting 1,5-syn-(E)-Diols: Application to the Synthesis of the C(23)-C(40) Fragment of Tetrafibricin.

Authors:  Philippe Nuhant; Jeremy Kister; Ricardo Lira; Achim Sorg; William R Roush
Journal:  Tetrahedron       Date:  2011-09-02       Impact factor: 2.457

4.  Synthesis of Bioactive Natural Products by Asymmetric syn- and anti-Aldol Reactions.

Authors:  Arun K Ghosh; Zachary L Dawson
Journal:  Synthesis (Stuttg)       Date:  2009-09       Impact factor: 3.157

5.  Enantioselective synthesis of 2-methyl-1,2-syn- and 2-methyl-1,2-anti-3-butenediols via allene hydroboration-aldehyde allylboration reaction sequences.

Authors:  Ming Chen; Masaki Handa; William R Roush
Journal:  J Am Chem Soc       Date:  2009-10-21       Impact factor: 15.419

6.  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 7.  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

8.  Concerning the selective protection of (Z)-1,5-syn-ene-diols and (E)-1,5-anti-ene-diols as allylic triethylsilyl ethers.

Authors:  Jacqueline D Hicks; Chan Woo Huh; Ashley D Legg; William R Roush
Journal:  Org Lett       Date:  2007-11-21       Impact factor: 6.005

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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