Synthesis of chiloscyphones and the biological activities of their synthetic intermediates against methicillin-resistant Staphylococcus aureus (MRSA)

Junichi Shiina, Rika Obata, Hiroshi Tomoda, Shigeru Nishiyama

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The total syntheses of chiloscyphone (1) and isochiloscyphone (2) have been achieved. Furthermore, the synthetic intermediate 5 shows biological activity against methicillin-resistant Staphyrococcus aureus, and compounds 5, 17, and 18, display imipenem-type activity. The tricyclic lactone framework, which includes an α,β-unsaturated ketone moiety, might play a crucial role in the anti-MRSA activity.

Original languageEnglish
Pages (from-to)2362-2370
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number10
DOIs
Publication statusPublished - 2006 May 12

Keywords

  • Antimicrobial activity
  • Bioorganic chemistry
  • Cyclization
  • MRSA
  • Medicinal chemistry
  • Natural products

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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