瑞香 cyclidin A 的合成研究：BCD 环系的对映体控制构建。
Synthetic studies on daphnicyclidin A: enantiocontrolled construction of the BCD ring system.
作者信息
Ikeda Shuhei, Shibuya Masatoshi, Kanoh Naoki, Iwabuchi Yoshiharu
机构信息
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Sendai 980-8578, Japan.
出版信息
Org Lett. 2009 Apr 16;11(8):1833-6. doi: 10.1021/ol9003405.
PMID:19320481
Abstract
An enantiocontrolled entry to the tricyclic core of daphnicyclidin A with five chiral centers including an all-carbon quaternary center is reported. The synthesis features a highly diastereoselective conjugate addition of nitromethane, an Ireland-Claisen rearrangement, and a tandem acyliminium/Mannich-type reaction.
摘要
报道了一种对映体控制的方法来构建含有五个手性中心（包括一个全碳季碳中心）的瑞香环丁烷A三环核心结构。该合成方法的特点包括硝基甲烷的高度非对映选择性共轭加成、爱尔兰-克莱森重排以及串联酰亚胺离子/曼尼希型反应。
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