Synthesis, crystal structure and antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes from 2,3-dihydroperoxy-2-phenylnorbornane

Kevin J. McCullough, Yuji Nonami, Araki Masuyama, Masatomo Nojima, Hye Sook Kim, Yusuke Wataya

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34 Citations (Scopus)

Abstract

Photooxygenation of 2-phenylnorbornene 1 in the presence of 30% aqueous hydrogen peroxide in acetonitrile afforded the labile 1,2-bis-hydroperoxide 3 which could be cycloalkylated to provide the tricyclic peroxides 5, albeit in low yield, on treatment with silver oxide and a 1,?-diiodoalkane. Trimethylsilylation of 3, followed by TMSOTf-catalyzed cyclocondensation with carbonyl compounds led to the formation of the tricyclic peroxides 8 containing a 1,2,4,5-tetroxepane structure. The structures of two novel tricyclic peroxides 5a and 8a were unambiguously determined by the X-ray crystallographic analysis.

Original languageEnglish
Pages (from-to)9151-9155
Number of pages5
JournalTetrahedron Letters
Volume40
Issue number51
Publication statusPublished - 17 Dec 1999

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    McCullough, K. J., Nonami, Y., Masuyama, A., Nojima, M., Kim, H. S., & Wataya, Y. (1999). Synthesis, crystal structure and antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes from 2,3-dihydroperoxy-2-phenylnorbornane. Tetrahedron Letters, 40(51), 9151-9155.