Library of biphenyl privileged substructures using a safety-catch linker approach

Severinsen, Rune, Bourne, Gregory T., Tran, Tran T., Ankersen, Michael, Begtrup, Mikael and Smythe, Mark L. (2008) Library of biphenyl privileged substructures using a safety-catch linker approach. Journal of Combinatorial Chemistry, 10 4: 557-566. doi:10.1021/cc800006g


Author Severinsen, Rune
Bourne, Gregory T.
Tran, Tran T.
Ankersen, Michael
Begtrup, Mikael
Smythe, Mark L.
Title Library of biphenyl privileged substructures using a safety-catch linker approach
Journal name Journal of Combinatorial Chemistry   Check publisher's open access policy
ISSN 1520-4766
1520-4774
Publication date 2008-08-05
Sub-type Article (original research)
DOI 10.1021/cc800006g
Volume 10
Issue 4
Start page 557
End page 566
Total pages 10
Editor A. W. Czarnik
Place of publication Washington, D.C,, U.S.A.
Publisher American Chemical Society
Language eng
Subject 030401 Biologically Active Molecules
030503 Organic Chemical Synthesis
Abstract A biphenyl privileged structure library containing three attachment points were synthesized using a catecholbased safety-catch linker strategy. The method requires the attachment of a bromo-acid to the linker, followed by a Pd-catalyzed Suzuki cross-coupling reaction. Further derivatization, activation of the linker with strong acid and aminolysis afforded the respective products in high purity and good overall yield. To show the versatility of the synthesis, a 199-member library was generated. The library samples both conformational and chemical diversity about a well-known privileged substructure.© 2008 American Chemical Society
Keyword Solid phase synthesis
Privileged substructures
Q-Index Code C1
Q-Index Status Provisional Code

Document type: Journal Article
Sub-type: Article (original research)
Collections: Excellence in Research Australia (ERA) - Collection
Institute for Molecular Bioscience - Publications
 
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Created: Thu, 03 Sep 2009, 19:49:14 EST by Mr Andrew Martlew on behalf of Institute for Molecular Bioscience