Stereocontrolled total synthesis of (-)-kainic acid.
Stereocontrolled total synthesis of (-)-kainic acid.
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DOI：
10.1021/ol0631197
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发表时间：
2007-03
期刊：
影响因子：
5.2
通讯作者：
H. Sakaguchi;H. Tokuyama;T. Fukuyama
中科院分区：
文献类型：
--
作者：
H. Sakaguchi;H. Tokuyama;T. Fukuyama
[反应：见正文] 描述了(-)-红藻氨酸的立体控制全合成。通过丙烯酸酯衍生物的闭环复分解，然后对所得的具有高非对映选择性的α，β-不饱和内酯进行分子内迈克尔加成，构建了全官能化的三取代吡咯烷环。还开发了两种用于构建α，β-不饱和内酯的替代方案。
[reaction: see text] A stereocontrolled total synthesis of (-)-kainic acid is described. A fully functionalized trisubstituted pyrrolidine ring was constructed by ring-closing metathesis of an acrylate derivative followed by an intramolecular Michael addition of the resultant alpha,beta-unsaturated lactone with high diastereoselectivity. Two alternative protocols for the construction of the alpha,beta-unsaturated lactone were also developed.