Enantioselective Total Synthesis of (−)‐Hosieine A |
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| Authors: | Jie Ouyang Rui Yan Xianwei Mi Prof?Dr Ran Hong |
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| Institution: | 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 |
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| Abstract: | The first total synthesis of (?)‐hosieine A was accomplished and features an unprecedented nitroso–ene cyclization to construct the 2‐azabicyclo3.2.1]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. |
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| Keywords: | ene reaction hyperconjugation receptors ring‐closing metathesis total synthesis |
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