通过跨环狄尔斯-阿尔德策略全合成肯帕烷二萜的合成方法。

Synthetic approach toward the total synthesis of kempane diterpenes via transannular Diels-Alder strategy.

作者信息

Caussanel Franck, Wang Keyan, Ramachandran Sreekanth A, Deslongchamps Pierre

机构信息

Laboratoire de Synthèse Organique, Département de Chimie, Institut de Pharmacologie, Université de Sherbrooke, Sherbrooke, Québec J1H 5N4, Canada.

出版信息

J Org Chem. 2006 Sep 15;71(19):7370-7. doi: 10.1021/jo061230k.

DOI:10.1021/jo061230k

PMID:16958532

Abstract

Total syntheses of two new (+/-)-kempane derivatives 30 and 47 were achieved with transannular Diels-Alder reaction (TADA) serving as the key step for the stereoselective formation of tricyclic [6.6.5] system 3. This synthetic approach also reveals that the geometry of the C3 group of such a tricyclic system plays an important role for the formation of the seven-membered kempane skeleton.

摘要

通过跨环狄尔斯-阿尔德反应（TADA）实现了两种新的（±）-坎帕烷衍生物30和47的全合成，该反应是立体选择性形成三环[6.6.5]体系3的关键步骤。这种合成方法还表明，这种三环体系中C3基团的几何结构对七元坎帕烷骨架的形成起着重要作用。