Synthesis and anti-malarial activity of yingzhaosu A analogues from unsaturated hydroperoxy acetals

Takahiro Tokuyasu; Araki Masuyama; Masatomo Nojima; Hye Sook Kim; Yusuke Wataya

doi:10.1016/S0040-4039(00)00372-5

Synthesis and anti-malarial activity of yingzhaosu A analogues from unsaturated hydroperoxy acetals

Takahiro Tokuyasu, Araki Masuyama, Masatomo Nojima, Hye Sook Kim, Yusuke Wataya

Research output: Contribution to journal › Article › peer-review

27 Citations (Scopus)

Abstract

Ozonolysis of a vinyl ether 2, prepared from dihydrocarvone 1 (a 1:4 mixture of cis- and trans-isomer), in methanol gave two isomeric unsaturated hydroperoxy acetals cis- and trans-3. Iodonium ion- or ozone-mediated cyclizations of the hydroperoxide cis-3 gave the corresponding yingzhaosu A analogues 4 and 6 in moderate yields. The peroxide 8, obtained by the Ag₂O- mediated methylation of 6, showed notable anti-malarial activity in vitro (IC₅₀=1.0 x 10^-7 M). (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	3145-3148
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4039(00)00372-5
Publication status	Published - Apr 22 2000

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Synthesis and anti-malarial activity of yingzhaosu A analogues from unsaturated hydroperoxy acetals",

abstract = "Ozonolysis of a vinyl ether 2, prepared from dihydrocarvone 1 (a 1:4 mixture of cis- and trans-isomer), in methanol gave two isomeric unsaturated hydroperoxy acetals cis- and trans-3. Iodonium ion- or ozone-mediated cyclizations of the hydroperoxide cis-3 gave the corresponding yingzhaosu A analogues 4 and 6 in moderate yields. The peroxide 8, obtained by the Ag2O- mediated methylation of 6, showed notable anti-malarial activity in vitro (IC50=1.0 x 10-7 M). (C) 2000 Elsevier Science Ltd.",

author = "Takahiro Tokuyasu and Araki Masuyama and Masatomo Nojima and Kim, {Hye Sook} and Yusuke Wataya",

note = "Funding Information: This work was supported in part by a Grant-in-Aid for Scientific Research on Priority Areas (10153238 and 10166211) from the Ministry of Education, Science, Culture and Sports of Japan.",

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T1 - Synthesis and anti-malarial activity of yingzhaosu A analogues from unsaturated hydroperoxy acetals

AU - Tokuyasu, Takahiro

AU - Masuyama, Araki

AU - Nojima, Masatomo

AU - Kim, Hye Sook

AU - Wataya, Yusuke

N1 - Funding Information: This work was supported in part by a Grant-in-Aid for Scientific Research on Priority Areas (10153238 and 10166211) from the Ministry of Education, Science, Culture and Sports of Japan.

PY - 2000/4/22

Y1 - 2000/4/22

N2 - Ozonolysis of a vinyl ether 2, prepared from dihydrocarvone 1 (a 1:4 mixture of cis- and trans-isomer), in methanol gave two isomeric unsaturated hydroperoxy acetals cis- and trans-3. Iodonium ion- or ozone-mediated cyclizations of the hydroperoxide cis-3 gave the corresponding yingzhaosu A analogues 4 and 6 in moderate yields. The peroxide 8, obtained by the Ag2O- mediated methylation of 6, showed notable anti-malarial activity in vitro (IC50=1.0 x 10-7 M). (C) 2000 Elsevier Science Ltd.

AB - Ozonolysis of a vinyl ether 2, prepared from dihydrocarvone 1 (a 1:4 mixture of cis- and trans-isomer), in methanol gave two isomeric unsaturated hydroperoxy acetals cis- and trans-3. Iodonium ion- or ozone-mediated cyclizations of the hydroperoxide cis-3 gave the corresponding yingzhaosu A analogues 4 and 6 in moderate yields. The peroxide 8, obtained by the Ag2O- mediated methylation of 6, showed notable anti-malarial activity in vitro (IC50=1.0 x 10-7 M). (C) 2000 Elsevier Science Ltd.

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JO - Tetrahedron Letters

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Synthesis and anti-malarial activity of yingzhaosu A analogues from unsaturated hydroperoxy acetals

Abstract

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