Department of Pharmaceutical Sciences, University of Connecticut, Storrs, Connecticut 06269, United States.
Org Lett. 2011 May 6;13(9):2433-5. doi: 10.1021/ol200706f. Epub 2011 Apr 1.
A rapid approach to the spirocyclic core of cyclopamine was achieved in four steps from 2-pentenyl-furan. A furan Diels-Alder reaction followed by a one-pot dehalogenation/amination sequence provides the oxabicyclic triene that upon treatment with Grubbs' catalyst undergoes smooth rearrangement to the tricyclic core.
从 2-戊烯基呋喃出发，经过四步反应即可快速构建环巴胺的螺环核心。呋喃 Diels-Alder 反应后，经一锅脱卤/胺化反应得到氧杂双环三烯，用 Grubbs 催化剂处理后可顺利重排为三环核心。
