title: Enantioselective Total Synthesis of (-)-Hosieine A.
abstract: 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.
authors.affiliation: 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.
authors.forename: Jie
authors.initials: J
authors.lastname: Ouyang
authors.affiliation: 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.
authors.forename: Rui
authors.initials: R
authors.lastname: Yan
authors.affiliation: 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.
authors.forename: Xianwei
authors.initials: X
authors.lastname: Mi
authors.affiliation: 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. rhong@sioc.ac.cn.
authors.forename: Ran
authors.initials: R
authors.lastname: Hong
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; C000607711:hosieine A
keywords: ene reaction; hyperconjugation; receptors; ring-closing metathesis; total synthesis