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

5 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

Fingerprint

Methicillin
staphylococcus
activity (biology)
Bioactivity
Imipenem
Lactones
synthesis
Ketones
ketones

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of chiloscyphones and the biological activities of their synthetic intermediates against methicillin-resistant Staphylococcus aureus (MRSA). / Shiina, Junichi; Obata, Rika; Tomoda, Hiroshi; Nishiyama, Shigeru.

In: European Journal of Organic Chemistry, No. 10, 12.05.2006, p. 2362-2370.

Research output: Contribution to journalArticle

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