title: Diastereoselective synthesis of cyclopentanoids: applications to the construction of the ABCD tetracyclic core of retigeranic acid A.
abstract: A concise and efficient approach for the construction of the tetracyclic carbon skeleton of retigeranic acid A is described. The key transformations include a novel Rh-catalyzed [3+2] cycloaddition of enyol to afford cyclopentanoid E, bearing two contiguous quaternary stereocenters at the bridgehead positions, and an intramolecular Pauson-Khand reaction to construct the advanced tetracyclic core structure of retigeranic acid A.
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055 (P. R. China).
authors.forename: Junlin
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055 (P. R. China).
authors.forename: Xiao
authors.initials: X
authors.lastname: Wang
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055 (P. R. China).
authors.forename: Shuang
authors.initials: S
authors.lastname: Li
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055 (P. R. China).
authors.forename: Dian
authors.initials: D
authors.lastname: Li
authors.affiliation: School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400030 (P. R. China).
authors.forename: Song
authors.initials: S
authors.lastname: Liu
authors.affiliation: School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400030 (P. R. China). lanyu@cqu.edu.cn.
authors.forename: Yu
authors.initials: Y
authors.lastname: Lan
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055 (P. R. China). gongjx@pku.edu.cn.
authors.forename: Jianxian
authors.initials: J
authors.lastname: Gong
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055 (P. R. 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 (P. R. 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 266003 (P. R. China). zyang@pku.edu.cn.
authors.forename: Zhen
authors.initials: Z
authors.lastname: Yang
mesh_terms: D002384:Catalysis; D003500:Cyclization; D061565:Cycloaddition Reaction; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; D011083:Polycyclic Compounds; C000606569:retigeranic acid A; D012238:Rhodium
keywords: Pauson-Khand reaction; [3+2] cycloaddition; natural products; quaternary stereocenters; retigeranic acids