摘要
R(+)-香茅醛的烯胺与丙烯酸乙酯反应,得2-(2′-乙氧羰基乙基)香茅醛。此产物用 Lewis 酸进行分子内烯反应,水解和内酯化后,得一由四个异构体组成的粗产物。此异构体的比例随反应条件和所用的 Lewis 酸不同而变化。经一系列反应,由此烯反应产物可得二个不同的酮-γ-内酯化合物,它们可望用作合成青蒿素类似物的中间体。其中一个γ-内酯8b 证明与一青蒿素降解产物一致,因此也就确定了它的立体化学。
The enamine of R(+)-citronellal was treated with ethyl acrylate to give 2-(2'-eth)(?)thy(?)-citronellal.The intramolecular ene reaction of the later was performed in the p(?) of Lewis acid.A crude product consisted of four isomers were obtained afterhydrolysis and lactonization.The ratio of isomers varied with the reaction condition andLewis acid u(?).(?)wo different ketone-γ-lactones,probably useful intermediate for the(?) of analogues of qinghaosu,was prepared via a series of reaction from the ene rea-ction (?).One γ-Inetone 8 b was identified with a degradation product of qinghaosuand hence its stereochemistry was established.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
1991年第5期488-493,共6页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金部份资助课题
关键词
烯反应
香茅醛
青蒿素
合成
Ene reaction,Citronellal,Qinghaosu,synthesis
