Synthetic methods for unsymmetrically-substituted 1,2,4,5-tetroxanes and of 1,2,4,5,7-pentoxocanes

Hye-Sook Kim, Kaoru Tsuchiya, Yasuharu Shibata, Yusuke Wataya, Yoshihiro Ushigoe, Araki Masuyama, Màsatomo Nojima, Kevin J. McCullough

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Abstract

Ozonolysis of vinyl ethers la-c in the presence of hydrogen peroxide in diethyl ether gave the corresponding 1,1-bis(hydroperoxide)s 2a-c. Subsequent trimethylsilylation, followed by the TMSOTf-catalyzed cyclocondensation with carbonyl compounds gave the unsymmetrically-substituted 1,2,4,5-tetroxanes 5-14. Similarly, the 1,2,4,5,7-pentoxocanes 18,19 were prepared by the reaction of an α,α′-bis(trimethylsilylperoxy) ether 17 and carbonyl compounds. The tetroxane 14 showed notable antimalarial activity in vitro and HI vivo.

Original languageEnglish
Pages (from-to)1867-1870
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number13
Publication statusPublished - 1999

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ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry

Cite this

Kim, H-S., Tsuchiya, K., Shibata, Y., Wataya, Y., Ushigoe, Y., Masuyama, A., Nojima, M., & McCullough, K. J. (1999). Synthetic methods for unsymmetrically-substituted 1,2,4,5-tetroxanes and of 1,2,4,5,7-pentoxocanes. Journal of the Chemical Society, Perkin Transactions 1, (13), 1867-1870.