Mechanism-based design of simple, symmetrical, easily prepared, potent antimalarial endoperoxides

Gary H. Posner, Dasong Wang, Lluïsa González, Xueliang Tao, Jared N. Cumming, Donna Klinedinst, Theresa A. Shapiro

Research output: Contribution to journalArticlepeer-review

Abstract

Mechanism-based design, two-step synthesis, and in vitro antimalarial testing showed thermally stable, crystalline, bicyclic endoperoxides 2a and 2b to be potent antimalarials. Their reduction by FeBr2 proceeds via oxy-radicals and then carbon radicals that undergo β-scission to form an alkene and a high-valent Fe=O species.

Original languageEnglish (US)
Pages (from-to)815-818
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number6
DOIs
StatePublished - Feb 5 1996

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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