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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82 Citations (Scopus)

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
DOIs
Publication statusPublished - Jan 1 1999

ASJC Scopus subject areas

  • Chemistry(all)

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