(-)-康洛因的全合成。
Total Synthesis of (-)-Conolutinine.
机构信息
Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University , 22 Xinong Road, Yangling 712100, Shaanxi, China.
State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases, Center of Drug Discovery, China Pharmaceutical University , 24 Tongjiaxiang, Nanjing 210009, China.
出版信息
Org Lett. 2015 Sep 18;17(18):4428-31. doi: 10.1021/acs.orglett.5b02046. Epub 2015 Aug 28.
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)2 was 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.
首次实现了（-）-康洛丁宁的对映选择性全合成，共 10 步。该合成以催化不对称溴环化反应构建三环中间体为特色，采用 Co(acac)2 催化的烯烃水合反应作为关键步骤，立体选择性地引入叔醇部分。基于该不对称全合成，（-）-康洛丁宁的绝对构型确定为（2S,5aS,8aS,13aR）。
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