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

Research output: Contribution to journalArticle

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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Peroxides
Antimalarials
Crystal structure
Hydrogen Peroxide
Carbonyl compounds
X rays

Cite this

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.
McCullough, Kevin J. ; Nonami, Yuji ; Masuyama, Araki ; Nojima, Masatomo ; Kim, Hye Sook ; Wataya, Yusuke. / Synthesis, crystal structure and antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes from 2,3-dihydroperoxy-2-phenylnorbornane. In: Tetrahedron Letters. 1999 ; Vol. 40, No. 51. pp. 9151-9155.
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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.",
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McCullough, KJ, Nonami, Y, Masuyama, A, Nojima, M, Kim, HS & Wataya, Y 1999, 'Synthesis, crystal structure and antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes from 2,3-dihydroperoxy-2-phenylnorbornane', Tetrahedron Letters, vol. 40, no. 51, pp. 9151-9155.

Synthesis, crystal structure and antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes from 2,3-dihydroperoxy-2-phenylnorbornane. / McCullough, Kevin J.; Nonami, Yuji; Masuyama, Araki; Nojima, Masatomo; Kim, Hye Sook; Wataya, Yusuke.

In: Tetrahedron Letters, Vol. 40, No. 51, 17.12.1999, p. 9151-9155.

Research output: Contribution to journalArticle

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AU - Kim, Hye Sook

AU - Wataya, Yusuke

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Y1 - 1999/12/17

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AB - 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.

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