Yingzhaosu A analogues: Synthesis by the ozonolysis of unsaturated hydroperoxides, structural analysis and determination of anti-malarial activity

Takahiro Tokuyasu; Araki Masuyama; Masatomo Nojima; Kevin J. McCullough; Hye Sook Kim; Yusuke Wataya

doi:10.1016/S0040-4020(01)00557-9

Yingzhaosu A analogues: Synthesis by the ozonolysis of unsaturated hydroperoxides, structural analysis and determination of anti-malarial activity

Takahiro Tokuyasu
, Araki Masuyama
, Masatomo Nojima
, Kevin J. McCullough
, Hye Sook Kim
, Yusuke Wataya

School of Engineering & Physical Sciences

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

39 Citations (Scopus)

Abstract

Ozone-mediated cyclization of a series of unsaturated hydroperoxides 7, prepared from dienes 2, afforded the corresponding yingzhaosu A analogues 9 in moderate to high yield. X-Ray crystallographic analysis of two yingzhaosu A analogues, endo-9f and 13, showed that the 2,3-dioxabicyclo[3.3.1]nonane system adopts a chair-boat arrangement. Subsequent treatment of endoperoxides 9 with Ag₂O/MeI afforded the expected methyldioxy-substituted cyclic peroxides 14, several of which showed notable anti-malarial activity against P. falciparum in vitro. © 2001 Elsevier Science Ltd.

Original language	English
Pages (from-to)	5979-5989
Number of pages	11
Journal	Tetrahedron
Volume	57
Issue number	28
DOIs	https://doi.org/10.1016/S0040-4020(01)00557-9
Publication status	Published - 9 Jul 2001

Keywords

Anti-malarial activity
Ozone-mediated cyclization
Unsaturated hydroperoxides
Yingzhaosu A analogues

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10.1016/S0040-4020(01)00557-9

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title = "Yingzhaosu A analogues: Synthesis by the ozonolysis of unsaturated hydroperoxides, structural analysis and determination of anti-malarial activity",

abstract = "Ozone-mediated cyclization of a series of unsaturated hydroperoxides 7, prepared from dienes 2, afforded the corresponding yingzhaosu A analogues 9 in moderate to high yield. X-Ray crystallographic analysis of two yingzhaosu A analogues, endo-9f and 13, showed that the 2,3-dioxabicyclo[3.3.1]nonane system adopts a chair-boat arrangement. Subsequent treatment of endoperoxides 9 with Ag2O/MeI afforded the expected methyldioxy-substituted cyclic peroxides 14, several of which showed notable anti-malarial activity against P. falciparum in vitro. {\textcopyright} 2001 Elsevier Science Ltd.",

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author = "Takahiro Tokuyasu and Araki Masuyama and Masatomo Nojima and McCullough, \{Kevin J.\} and Kim, \{Hye Sook\} and Yusuke Wataya",

year = "2001",

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doi = "10.1016/S0040-4020(01)00557-9",

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T1 - Yingzhaosu A analogues

T2 - Synthesis by the ozonolysis of unsaturated hydroperoxides, structural analysis and determination of anti-malarial activity

AU - Tokuyasu, Takahiro

AU - Masuyama, Araki

AU - Nojima, Masatomo

AU - McCullough, Kevin J.

AU - Kim, Hye Sook

AU - Wataya, Yusuke

PY - 2001/7/9

Y1 - 2001/7/9

N2 - Ozone-mediated cyclization of a series of unsaturated hydroperoxides 7, prepared from dienes 2, afforded the corresponding yingzhaosu A analogues 9 in moderate to high yield. X-Ray crystallographic analysis of two yingzhaosu A analogues, endo-9f and 13, showed that the 2,3-dioxabicyclo[3.3.1]nonane system adopts a chair-boat arrangement. Subsequent treatment of endoperoxides 9 with Ag2O/MeI afforded the expected methyldioxy-substituted cyclic peroxides 14, several of which showed notable anti-malarial activity against P. falciparum in vitro. © 2001 Elsevier Science Ltd.

AB - Ozone-mediated cyclization of a series of unsaturated hydroperoxides 7, prepared from dienes 2, afforded the corresponding yingzhaosu A analogues 9 in moderate to high yield. X-Ray crystallographic analysis of two yingzhaosu A analogues, endo-9f and 13, showed that the 2,3-dioxabicyclo[3.3.1]nonane system adopts a chair-boat arrangement. Subsequent treatment of endoperoxides 9 with Ag2O/MeI afforded the expected methyldioxy-substituted cyclic peroxides 14, several of which showed notable anti-malarial activity against P. falciparum in vitro. © 2001 Elsevier Science Ltd.

KW - Anti-malarial activity

KW - Ozone-mediated cyclization

KW - Unsaturated hydroperoxides

KW - Yingzhaosu A analogues

UR - https://www.scopus.com/pages/publications/0035833052

U2 - 10.1016/S0040-4020(01)00557-9

DO - 10.1016/S0040-4020(01)00557-9

M3 - Article

SN - 0040-4020

VL - 57

SP - 5979

EP - 5989

JO - Tetrahedron

JF - Tetrahedron

IS - 28

ER -

Yingzhaosu A analogues: Synthesis by the ozonolysis of unsaturated hydroperoxides, structural analysis and determination of anti-malarial activity

Abstract

Keywords

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