Synthesis, Fe(II)-induced degradation, and antimalarial activities of 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes: Direct evidence for nucleophilic O-1,2-aryl shifts

Masaki Kamata, Motoko Ohta, Ken Ichi Komatsu, Hye Sook Kim, Yusuke Wataya

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

1,5-Diaryl-6,7-dioxabicyclo[3.2.2]nonanes 1a-d (1a: Ar=p-FC6H4, 1b: Ar=Ph, 1c: Ar=p-MeC6H4, 1d: Ar=p-MeOC6H4) were prepared by a modified method of photo-electron transfer oxygenation, and the reactions of 1 with FeBr2 were investigated under various conditions. The Fe(II)-induced degradation of 1 afforded various rearrangement products and fragmentation products through competitive single electron transfer (SET) and Lewis acid pathways. Direct evidence for the O-1,2-aryl shift was obtained by the isolation of rearrangement products, 1-aryloxy-5-aryl-8-oxabicyclo[3.2.1]octanes 8. The degradation mechanism was proposed and the in vitro antimalarial activities were also evaluated.

Original languageEnglish
Pages (from-to)2063-2067
Number of pages5
JournalTetrahedron Letters
Volume43
Issue number11
DOIs
Publication statusPublished - Mar 11 2002

Keywords

  • 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes
  • Antimalarial activity
  • Cyclic peroxides
  • FeBr
  • Fragmentation
  • O-1,2-aryl shift
  • Reaction mechanism
  • Rearrangement

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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