title: Asymmetric Total Synthesis of (-)-Maoecrystal V.
abstract: The asymmetric total synthesis of (-)-maoecrystal V, a novel cytotoxic pentacyclic ent-kaurane diterpene, has been accomplished. Key steps of the current strategy involve an early-stage semipinacol rearrangement reaction for the construction of the C10 quaternary stereocenter, a rhodium-catalyzed intramolecular O-H insertion reaction, and a sequential Wessely oxidative dearomatization/intramolecular Diels-Alder reaction to forge the pentacyclic framework of maoecrystal V.
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055, China.
authors.forename: Wei-bin
authors.initials: WB
authors.lastname: Zhang
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055, China.
authors.forename: Wen-bin
authors.initials: WB
authors.lastname: Shao
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055, China.
authors.forename: Fu-zhuo
authors.initials: FZ
authors.lastname: Li
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055, China. gongjx@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. zyang@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. zyang@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, China. zyang@pku.edu.cn.
authors.forename: Zhen
authors.initials: Z
authors.lastname: Yang
mesh_terms: D002384:Catalysis; D061565:Cycloaddition Reaction; D053138:Cyclohexenes / Q000737:chemistry; D003603:Cytotoxins / Q000138:chemical synthesis* / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D010084:Oxidation-Reduction; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D053138:Cyclohexenes; D003603:Cytotoxins; D004224:Diterpenes; C519041:semipinacol; D012238:Rhodium; C545599:maoecrystal V
keywords: asymmetric synthesis; diels-alder reaction; rhodium; semi-pinacol rearrangement; total synthesis