Tetrahedron

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

T Tokuyasu, A Masuyama, M Nojima, KJ McCullough…

Index: Tokuyasu, Takahiro; Masuyama, Araki; Nojima, Masatomo; McCullough, Kevin J; Kim, Hye-Sook; Wataya, Yusuke Tetrahedron, 2001 , vol. 57, # 28 p. 5979 - 5989

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Citation Number: 30

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- ...