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 journalArticle

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 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

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Tetraoxanes
Carbonyl compounds
Ether
Hydrogen Peroxide
Antimalarials

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Kim, H. S., Tsuchiya, K., Shibata, Y., Wataya, Y., Ushigoe, Y., Masuyama, A., ... McCullough, K. J. (1999). Synthetic methods for unsymmetrically-substituted 1,2,4,5-tetroxanes and of 1,2,4,5,7-pentoxocanes. Journal of the Chemical Society, Perkin Transactions 1, (13), 1867-1870.
Kim, Hye Sook ; Tsuchiya, Kaoru ; Shibata, Yasuharu ; Wataya, Yusuke ; Ushigoe, Yoshihiro ; Masuyama, Araki ; Nojima, Màsatomo ; McCullough, Kevin J. / Synthetic methods for unsymmetrically-substituted 1,2,4,5-tetroxanes and of 1,2,4,5,7-pentoxocanes. In: Journal of the Chemical Society, Perkin Transactions 1. 1999 ; No. 13. pp. 1867-1870.
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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 a,a'-bis(trimethylsilylperoxy) ether 17 and carbonyl compounds. The tetroxane 14 showed notable antimalarial activity in vitro and HI vivo.",
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Kim, HS, Tsuchiya, K, Shibata, Y, Wataya, Y, Ushigoe, Y, Masuyama, A, Nojima, M & McCullough, KJ 1999, 'Synthetic methods for unsymmetrically-substituted 1,2,4,5-tetroxanes and of 1,2,4,5,7-pentoxocanes', Journal of the Chemical Society, Perkin Transactions 1, no. 13, pp. 1867-1870.

Synthetic methods for unsymmetrically-substituted 1,2,4,5-tetroxanes and of 1,2,4,5,7-pentoxocanes. / Kim, Hye Sook; Tsuchiya, Kaoru; Shibata, Yasuharu; Wataya, Yusuke; Ushigoe, Yoshihiro; Masuyama, Araki; Nojima, Màsatomo; McCullough, Kevin J.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 13, 1999, p. 1867-1870.

Research output: Contribution to journalArticle

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T1 - Synthetic methods for unsymmetrically-substituted 1,2,4,5-tetroxanes and of 1,2,4,5,7-pentoxocanes

AU - Kim, Hye Sook

AU - Tsuchiya, Kaoru

AU - Shibata, Yasuharu

AU - Wataya, Yusuke

AU - Ushigoe, Yoshihiro

AU - Masuyama, Araki

AU - Nojima, Màsatomo

AU - McCullough, Kevin J.

PY - 1999

Y1 - 1999

N2 - 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.

AB - 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.

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M3 - Article

SP - 1867

EP - 1870

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

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