Mergott Dustin J, Zuend Stephan J, Jacobsen Eric N
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Org Lett. 2008 Mar 6;10(5):745-8. doi: 10.1021/ol702781q. Epub 2008 Feb 8.
The total synthesis of (+)-yohimbine was achieved in 11 steps and 14% overall yield. The absolute configuration was established through a highly enantioselective thiourea-catalyzed acyl-Pictet-Spengler reaction, and the remaining 4 stereocenters were set simultaneously in a substrate-controlled intramolecular Diels-Alder reaction.
(+)-育亨宾的全合成以11步反应完成,总产率为14%。其绝对构型通过高度对映选择性的硫脲催化酰基-Pictet-Spengler反应确定,其余4个立体中心在底物控制的分子内Diels-Alder反应中同时构建。