Sethofer Steven G, Staben Steven T, Hung Olivia Y, Toste F Dean
Department of Chemistry, University of California, Berkeley, Berkeley, California 94720-1460, USA.
Org Lett. 2008 Oct 2;10(19):4315-8. doi: 10.1021/ol801760w. Epub 2008 Aug 30.
The gold(I)-catalyzed cycloisomerization of enynes containing an embedded cyclopropane unit leads selectively to the formation of ring systems containing the cyclopropylmethyl cation. A subsequent Wagner-Merwein shift provides diastereomerically pure fused cyclobutanes. The utility of this methodology for the rapid assembly of polycyclic ring systems is illustrated by the total synthesis of the angular triquinane ventricosene.
含有内嵌环丙烷单元的烯炔的金（I）催化环异构化反应选择性地导致含有环丙基甲基阳离子的环系的形成。随后的瓦格纳-梅尔外因重排提供非对映体纯的稠合环丁烷。角型三环烷ventricosene的全合成证明了这种方法在多环环系快速组装中的实用性。
