An efficient synthesis of bridged-bicyclic peroxides structurally related to antimalarial yingzhaosu A based on radical co-oxygenation of thiols and monoterpenes

被引：38

作者：

Korshin, EE

Hoos, R

Szpilman, AM

Konstantinovski, L

Posner, GH

Bachi, MD ^{[1
]}

机构：

[1] Weizmann Inst Sci, Dept Organ Chem, IL-76100 Rehovot, Israel

[2] Johns Hopkins Univ, Dept Chem, Sch Arts & Sci, Baltimore, MD 21218 USA

来源：

TETRAHEDRON | 2002年 / 58卷 / 12期

关键词：

antimalarial peroxides; free radicals; multi-component reaction; sequential reactions; thiol olefin co-oxygenation reaction;

D O I：

10.1016/S0040-4020(02)00126-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of beta-sulfenyl endoperoxides 9 was achieved by a four component sequential free radical reaction based on the application of the thiol-olefin-co-oxygenation reaction to monoterpenes, followed by in situ treatment with triphenylphosphine. beta-Sulfenyl endoperoxides 9 were oxidized with m-CPBA to beta-sulfonyl endoperoxides 10. This process provides an efficient method for the preparation of peroxides containing the 2,3-dioxabicyclo[3.3.1]nonane system (2) characteristic of antimalarial agents of the yingzhaosu A (3) family. A simple NMR diagnostic tool for the identification of stereoisomers is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：2449 / 2469

页数：21

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