title: Total Synthesis of (-)-Conolutinine.
abstract: 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.
authors: 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.
authors: Xiangyang
authors: X
authors: Feng
authors: 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.
authors: Guangde
authors: G
authors: Jiang
authors: 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.
authors: Zilei
authors: Z
authors: Xia
authors: 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.
authors: Jiadong
authors: J
authors: Hu
authors: State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.
authors: Xiaolong
authors: X
authors: Wan
authors: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University , 22 Xinong Road, Yangling 712100, Shaanxi, China.
authors: Jin-Ming
authors: JM
authors: Gao
authors: 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.
authors: Yisheng
authors: Y
authors: Lai
authors: 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 Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.
authors: Weiqing
authors: W
authors: Xie
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008296:Malaysia; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D014363:Tryptamines
chemical_list: D000475:Alkenes; D006842:Hydrocarbons, Brominated; D026121:Indole Alkaloids; D014363:Tryptamines; C000603898:conolutinine; C030820:tryptamine