Synthesis of the phenylpyridal scaffold as a helical peptide mimetic

Bourne, Gregory T., Kuster, Daniel J. and Marshall, Garland R. (2010) Synthesis of the phenylpyridal scaffold as a helical peptide mimetic. Chemistry: A European Journal, 16 28: 8439-8445. doi:10.1002/chem.201000315


Author Bourne, Gregory T.
Kuster, Daniel J.
Marshall, Garland R.
Title Synthesis of the phenylpyridal scaffold as a helical peptide mimetic
Journal name Chemistry: A European Journal   Check publisher's open access policy
ISSN 0947-6539
1521-3765
Publication date 2010-07-26
Sub-type Article (original research)
DOI 10.1002/chem.201000315
Open Access Status
Volume 16
Issue 28
Start page 8439
End page 8445
Total pages 7
Place of publication Weinheim, Germany
Publisher Wiley - V C H Verlag GmbH & Co. KGaA
Language eng
Abstract Phenylpyridal- and phenyldipyridal-based scaffolds have been designed and synthesized as novel helical peptide mimetics. The synthesis required optimisation and selective alkylation in producing 2,6-functionalized 3-hydroxypyridine derivatives for a convergent scheme. The pyridine analogues were coupled by a series of Suzuki/Stille types cross-coupling reactions. A series of biaryl and ter-aryl substituted heterocycles were produced. The synthetic approach was concise and high yielding allowing large variability at the wanted sidechain attachment points. A number of compounds were synthesised to show the versatility of the strategy.
Keyword Alkylation
Biaryls
Cross-coupling
Helical structures
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: Institute for Molecular Bioscience - Publications
 
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