title: Enantioselective Approach to (-)-Hamigeran B and (-)-4-Bromohamigeran B via Catalytic Asymmetric Hydrogenation of Racemic Ketone To Assemble the Chiral Core Framework.
abstract: A new strategy featuring an iridium-catalyzed asymmetric hydrogenation of a racemic ketone via dynamic kinetic resolution to generate a cyclopentanol with three contiguous stereocenters and a SmI2-promoted pinacol coupling to install the six-membered ring with correct stereochemistry has been described for the enantioselective total synthesis of (-)-hamigeran B (19 steps, 10.6% overall yield) and (-)-4-bromohamigeran B (19 steps, 12.3% overall yield).
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry and ‡Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, China.
authors.forename: Han
authors.initials: H
authors.lastname: Lin
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry and ‡Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, China.
authors.forename: Li-Jun
authors.initials: LJ
authors.lastname: Xiao
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry and ‡Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, China.
authors.forename: Min-Jie
authors.initials: MJ
authors.lastname: Zhou
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry and ‡Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, China.
authors.forename: Hong-Ming
authors.initials: HM
authors.lastname: Yu
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry and ‡Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, China.
authors.forename: Jian-Hua
authors.initials: JH
authors.lastname: Xie
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry and ‡Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, China.
authors.forename: Qi-Lin
authors.initials: QL
authors.lastname: Zhou
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry; D006865:Hydrogenation; D007495:Iridium / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C556079:4-bromohamigeran B; D001688:Biological Products; D003517:Cyclopentanes; D007659:Ketones; D009285:Naphthoquinones; C483756:hamigeran B; C016327:cyclopentanol; D007495:Iridium