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

32 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,ω-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 - Dec 17 1999

Fingerprint

Peroxides
Antimalarials
Crystal structure
Hydrogen Peroxide
Carbonyl compounds
X-Rays
X rays

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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

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.
@article{837154a6ae2643f2876ce95e8082cb7d,
title = "Synthesis, crystal structure and antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes from 2,3-dihydroperoxy-2-phenylnorbornane",
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,ω-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.",
author = "McCullough, {Kevin J.} and Yuji Nonami and Araki Masuyama and Masatomo Nojima and Hye-Sook Kim and Yusuke Wataya",
year = "1999",
month = "12",
day = "17",
language = "English",
volume = "40",
pages = "9151--9155",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "51",

}

TY - JOUR

T1 - Synthesis, crystal structure and antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes from 2,3-dihydroperoxy-2-phenylnorbornane

AU - McCullough, Kevin J.

AU - Nonami, Yuji

AU - Masuyama, Araki

AU - Nojima, Masatomo

AU - Kim, Hye-Sook

AU - Wataya, Yusuke

PY - 1999/12/17

Y1 - 1999/12/17

N2 - 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,ω-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.

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,ω-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.

UR - http://www.scopus.com/inward/record.url?scp=0033579626&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033579626&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0033579626

VL - 40

SP - 9151

EP - 9155

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 51

ER -