Convergent approach to the maduropeptin chromophore: Aryl ether formation of (R)-3-aryl-3-hydroxypropanamide and cyclization of macrolactam

Nobuki Kato, Satoshi Shimamura, Safraz Khan, Fumiyo Takeda, Yoko Kikai, Masahiro Hirama

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Efficient enantioselective syntheses of the functionalized phenol and diethynylcyclopentene moiety of the maduropeptin chromophore were achieved. Their CsF-mediated coupling yielded a sterically congested aryl propargyl ether. The subsequent intramolecular Sonogashira coupling reaction between the vinyl iodide and diethynyl groups occurred at the appropriate position to yield a macrolactam, which was accompanied by Pd-mediated enyne-yne benzannulation.

Original languageEnglish
Pages (from-to)3161-3172
Number of pages12
JournalTetrahedron
Volume60
Issue number14
DOIs
Publication statusPublished - 2004 Mar 29

Keywords

  • Aryl ether formation
  • Benzannulation
  • Enantioselective synthesis
  • Macrolactam
  • Maduropeptin chromophore

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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