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

Research output: Contribution to journalArticlepeer-review

86 Citations (Scopus)


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 a,a'-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


Dive into the research topics of 'Synthetic methods for unsymmetrically-substituted 1,2,4,5-tetroxanes and of 1,2,4,5,7-pentoxocanes'. Together they form a unique fingerprint.

Cite this