Enantioselective Total Synthesis of (-)-HosieineA
Enantioselective Total Synthesis of (-)-HosieineA
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DOI：
10.1002/anie.201505251
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发表时间：
2015-09-07
影响因子：
16.6
通讯作者：
Hong, Ran
中科院分区：
文献类型：
--
作者：
Ouyang, Jie;Yan, Rui;Hong, Ran
首次完成了（-）-玫瑰茄碱A的全合成，其特征在于前所未有的亚硝基苯环化以构建2-氮杂双环[3.2.1]辛烷环系统。膦使能的立体选择性溴氢化提供了有趣的机制的见解反马尔可夫尼科夫过程。还值得注意的是在由Et 3B/空气引发的容易的自由基脱溴中在C9处保留了立体化学。
The first total synthesis of (-)-hosieineA was accomplished and features an unprecedented nitroso-ene cyclization to construct the 2-azabicyclo[3.2.1]octane ring system. Phosphine-enabled stereoselective bromohydrination provided interesting mechanistic insights into the anti-Markovnikov process. Also noteworthy is the retention of stereochemistry at C9 in the facile radical debromination initiated by Et3B/air.