化学
自动氧化
醛
臭氧
臭氧分解
烯丙基重排
过氧化氢
过氧化物
烯醇
立体化学
有机化学
激进的
催化作用
作者
Lai‐King Sy,Geoffrey D. Brown
出处
期刊:Tetrahedron
[Elsevier]
日期:2002-01-01
卷期号:58 (5): 897-908
被引量:113
标识
DOI:10.1016/s0040-4020(01)01193-0
摘要
Dihydroartemisinic acid undergoes slow spontaneous autoxidation to artemisinin and other natural products, which have been reported from the medicinal plant Artemisia annua. The mechanism of this complex transformation is shown to involve four steps: (i) initial reaction of the Δ4,5-double bond of dihydroartemisinic acid with molecular oxygen, (ii) Hock cleavage of the resulting tertiary allylic hydroperoxide; (iii) oxygenation of the enol product from Hock cleavage; and (iv) cyclization of the resulting vicinal hydroperoxyl-aldehyde to the 1,2,4-trioxane system of artemisinin.
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