An efficient synthesis of bridged-bicyclic peroxides structurally related to antimalarial yingzhaosu A based on radical co-oxygenation of thiols and monoterpenes

Edward E. Korshin, Roland Hoos, Alex M. Szpilman, Leonid Konstantinovski, Gary H. Posner, Mario D. Bachi

Research output: Contribution to journalArticlepeer-review

48 Scopus citations

Abstract

Synthesis of β-sulfenyl endoperoxides 9 was achieved by a four component sequential free radical reaction based on the application of the thiol-olefin-co-oxygenation reaction to monoterpenes, followed by in situ treatment with triphenylphosphine. β-Sulfenyl endoperoxides 9 were oxidized with m-CPBA to β-sulfonyl endoperoxides 10. This process provides an efficient method for the preparation of peroxides containing the 2,3-dioxabicyclo[3.3.1]nonane system (2) characteristic of antimalarial agents of the yingzhaosu A (3) family. A simple NMR diagnostic tool for the identification of stereoisomers is described.

Original languageEnglish
Pages (from-to)2449-2469
Number of pages21
JournalTetrahedron
Volume58
Issue number12
DOIs
StatePublished - 18 Mar 2002
Externally publishedYes

Keywords

  • Antimalarial peroxides
  • Free radicals
  • Multi-component reaction
  • Sequential reactions
  • Thiol olefin co-oxygenation reaction

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