title: Gold-Catalyzed Intramolecular Tandem Cyclization of Indole-Ynamides: Diastereoselective Synthesis of Spirocyclic Pyrrolidinoindolines.
abstract: A gold-catalyzed intramolecular tandem cyclization of indole-ynamide affords tetracyclic spirocyclic pyrrolidinoindoline bearing an all-carbon quaternary stereocentre in a single step; however, when the reaction was carried out in the presence of BF3 ⋅Et2 O, the corresponding tricyclic spirocyclic pyrrolidinoindoline-based enones are produced through a key 1,5-hydride shift. The developed chemistry provides a diastereoselective and straightforward entry to structurally diverse polycylic pyrrolidinoindolines from indole-ynamides in one-pot reactions under mild conditions.
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University, Shenzhen Graduate School, Shenzhen, 518055, China.
authors.forename: Nan
authors.initials: N
authors.lastname: Zheng
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University, Shenzhen Graduate School, Shenzhen, 518055, China.
authors.forename: Yuan-Yuan
authors.initials: YY
authors.lastname: Chang
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University, Shenzhen Graduate School, Shenzhen, 518055, China.
authors.forename: Li-Jie
authors.initials: LJ
authors.lastname: Zhang
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University, Shenzhen Graduate School, Shenzhen, 518055, China. zyang@pku.edu.cn.
authors.forename: Jian-Xian
authors.initials: JX
authors.lastname: Gong
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University, Shenzhen Graduate School, Shenzhen, 518055, China. gongjx@pku.edu.cn.|Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and, Beijing National Laboratory for Molecular Science (BNLMS), Peking- Tsinghua Center for Life Sciences, Peking University, Beijing, 100871, China. gongjx@pku.edu.cn.|Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao, 266003, China. gongjx@pku.edu.cn.
authors.forename: Zhen
authors.initials: Z
authors.lastname: Yang
mesh_terms: D000470:Alkaloids / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D007211:Indoles; D013141:Spiro Compounds; D006046:Gold
keywords: 1,5-hydride shif; cyclizationt; diastereoselectivity; gold; spirocyclic pyrrolidinoindoline