title: Total synthesis of (±)-decinine via an oxidative biaryl coupling with defined axial chirality.
abstract: The total synthesis of (±)-decinine has been achieved. The key steps in the synthesis involved the formation of lasubine II via a gold catalyzed annulation of 1-(but-3-yn-1-yl)piperidine and the formation of the 12-membered ring of decinine (1) with complementary atropselectivity via a VOF3-mediated oxidative biaryl coupling reaction.
authors: Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences at College of Chemistry of Peking University, Chengfu Road, 202, Beijing, China, 100871, and The Comprehensive AIDS Research Center, School of Life Science and School of Medicine, Tsinghua University, Beijing 100084, China.
authors: Zhen-Hua
authors: ZH
authors: Shan
authors: Ji
authors: J
authors: Liu
authors: Ling-Min
authors: LM
authors: Xu
authors: Ye-Feng
authors: YF
authors: Tang
authors: Jia-Hua
authors: JH
authors: Chen
authors: Zhen
authors: Z
authors: Yang
mesh_terms: D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D058451:Oxidative Coupling; D013237:Stereoisomerism
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; C588316:decinine; D006046:Gold