CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry (CAS), 345 Lingling Road, Shanghai 200032 (China) http://honggroup.sioc.ac.cn.
Angew Chem Int Ed Engl. 2015 Sep 7;54(37):10940-3. doi: 10.1002/anie.201505251. Epub 2015 Jul 21.
The first total synthesis of (-)-hosieine A 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 Et3 B/air.
(-)-霍西因 A 的首次全合成得以实现，其中采用了前所未有的亚硝酮-ene 环化反应来构建 2-氮杂双环[3.2.1]辛烷环系。膦促进的立体选择性溴化反应为反马氏规则过程提供了有趣的机理见解。同样值得注意的是，在 Et3 B/空气引发的易进行的自由基脱溴反应中，C9 处的立体化学得以保留。
