Facile synthesis of 7-alkyl-1,2,3,4-tetrahydro-1,8-naphthyridines as arginine mimetics using a Horner-Wadsworth-Emmons-based approach

Rhys A. Lippa, John A. Murphy, Tim N. Barrett

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Integrin inhibitors based on the tripeptide sequence Arg-Gly-Asp (RGD) are potential therapeutics for the treatment of idiopathic pulmonary fibrosis (IPF). Herein, we describe an expeditious three-step synthetic sequence of Horner-Wadsworth-Emmons olefination, diimide reduction, and global deprotection to synthesise cores for these compounds in high yields (63-83% over 3 steps) with no need for chromatography. Key to this transformation is the phosphoramidate protecting group, which is stable to metalation steps.

Original languageEnglish
Pages (from-to)1617-1626
Number of pages10
JournalBeilstein Journal of Organic Chemistry
Volume16
DOIs
Publication statusPublished - 8 Jul 2020

Keywords

  • arginine
  • Horner-Wadsworth-Emmons
  • integrin
  • phosphoramidate
  • tetrahydronaphthyridine

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