Ikeda Shuhei, Shibuya Masatoshi, Kanoh Naoki, Iwabuchi Yoshiharu
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Sendai 980-8578, Japan.
Org Lett. 2009 Apr 16;11(8):1833-6. doi: 10.1021/ol9003405.
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.
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。
