Synthesis of antimalarial 1,2,4-trioxanes via photooxygenation of a chiral allylic alcohol

被引:71
作者
Griesbeck, AG
El-Idreesy, TT
Fiege, M
Brun, R
机构
[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany
[2] Swiss Trop Inst, CH-4002 Basel, Switzerland
关键词
D O I
10.1021/ol026916n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Photooxygenation of the chiral allylic alcohol 4-methyl-3-penten-2-ol (3) in nonpolar solvents and subsequent Lewis acid-catalyzed peroxyacetalization afforded a series of monocyclic and spirobicyclic 1,2,4-trioxanes (5, 6). Two products show significant anti-Malaria activity against Plasmodium falciparum when compared with chloroquine.
引用
收藏
页码:4193 / 4195
页数:3
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