Total Synthesis of (-)-Conolutinine
Total Synthesis of (-)-Conolutinine
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(-)-Conolutinine的全合成
DOI：
10.1021/acs.orglett.5b02046
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发表时间：
2015
期刊：
影响因子：
5.2
通讯作者：
Xie Weiqing
中科院分区：
文献类型：
--
作者：
Feng Xiangyang;Jiang Guangde;Xia Zilei;Hu Jiadong;Wan Xiaolong;Gao Jin-Ming;Lai Yisheng;Xie Weiqing
第一个对映选择性合成（-）-conolutinine是在10个步骤中完成的。该合成的特点是色胺的催化不对称溴环化形成三环中间体。Co（acac）2催化的烯烃水合反应也被用作非对映选择性引入叔醇部分的关键步骤。在此基础上，确定了（-）-conolutinine的绝对构型为（2S，5aS，8aS，13 aR）。
The first enantioselective synthesis of (−)-conolutinine was achieved in 10 steps. The synthesis featured a catalytic asymmetric bromocyclization of tryptamine to forge the tricycle intermediate. Hydration of an alkene catalyzed by Co(acac)2was also employed as a key step to diastereoselectively introduce the tertiary alcohol moiety. The absolute configuration of (−)-conolutinine was established to be (2S,5aS,8aS,13aR) based on this asymmetric total synthesis.