Synthesis of the phenylpyridal scaffold as a helical peptide mimetic

Gregory T. Bourne, Daniel J. Kuster, Garland R. Marshall

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

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.

Original languageEnglish
Pages (from-to)8439-8445
Number of pages7
JournalChemistry - A European Journal
Volume16
Issue number28
DOIs
StatePublished - Jul 26 2010

Keywords

  • Alkylation
  • Biaryls
  • Cross-coupling
  • Helical structures
  • Proteomimetics

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