Total synthesis of aurachins C, D, and L, and a structurally simplified analog of aurachin C

Masaru Enomoto, Wataru Kitagawa, Yoshiaki Yasutake, Hiroki Shimizu

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The quinoline antibiotics aurachins C, D, and L, and a structurally simplified analog of aurachin C were synthesized from 1-(2-nitrophenyl)butane-1,3-dione via reductive cyclizations of δ-nitro ketone intermediates, with zinc or iron as key steps. The results of antimicrobial tests indicate that the N-hydroxyquinolone nucleus mimics the electron carrier in the respiratory chain more strongly than the quinoline N-oxide nucleus.

Original languageEnglish
Pages (from-to)1324-1327
Number of pages4
JournalBioscience, Biotechnology and Biochemistry
Volume78
Issue number8
DOIs
Publication statusPublished - 2014 Jan 1
Externally publishedYes

Keywords

  • Aurachins
  • Quinoline antibiotics
  • Reductive cyclization

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

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