Yingzhaosu A analogues: Synthesis by the ozonolysis of unsaturated hydroperoxides, structural analysis and determination of anti-malarial activity

Takahiro Tokuyasu, Araki Masuyama, Masatomo Nojima, Kevin J. McCullough, Hye Sook Kim, Yusuke Wataya

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)

Abstract

Ozone-mediated cyclization of a series of unsaturated hydroperoxides 7, prepared from dienes 2, afforded the corresponding yingzhaosu A analogues 9 in moderate to high yield. X-Ray crystallographic analysis of two yingzhaosu A analogues, endo-9f and 13, showed that the 2,3-dioxabicyclo[3.3.1]nonane system adopts a chair-boat arrangement. Subsequent treatment of endoperoxides 9 with Ag2O/MeI afforded the expected methyldioxy-substituted cyclic peroxides 14, several of which showed notable anti-malarial activity against P. falciparum in vitro.

Original languageEnglish
Pages (from-to)5979-5989
Number of pages11
JournalTetrahedron
Volume57
Issue number28
DOIs
Publication statusPublished - Jul 9 2001

Keywords

  • Anti-malarial activity
  • Ozone-mediated cyclization
  • Unsaturated hydroperoxides
  • Yingzhaosu A analogues

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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