title: Highly enantioselective bromocyclization of tryptamines and its application in the synthesis of (-)-chimonanthine.
abstract: A shorter path: A highly enantioselective bromocyclization of tryptamine has been developed using an anionic chiral phase-transfer catalyst. This method provides a direct approach for preparing chiral 3-bromopyrroloindoline from tryptamine, which enables a four-step enantioselective synthesis of (-)-chimonanthine. PG=protecting group.
authors.affiliation: State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China). xiewq@sioc.ac.cn.
authors.forename: Weiqing
authors.initials: W
authors.lastname: Xie
authors.forename: Guangde
authors.initials: G
authors.lastname: Jiang
authors.forename: Huan
authors.initials: H
authors.lastname: Liu
authors.forename: Jiadong
authors.initials: J
authors.lastname: Hu
authors.forename: Xixian
authors.initials: X
authors.lastname: Pan
authors.forename: Hui
authors.initials: H
authors.lastname: Zhang
authors.forename: Xiaolong
authors.initials: X
authors.lastname: Wan
authors.forename: Yisheng
authors.initials: Y
authors.lastname: Lai
authors.forename: Dawei
authors.initials: D
authors.lastname: Ma
mesh_terms: D002384:Catalysis; D003500:Cyclization; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014363:Tryptamines / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D006842:Hydrocarbons, Brominated; D007211:Indoles; D011758:Pyrroles; D014363:Tryptamines; C521484:chimonanthine
keywords: asymmetric synthesis; chimonanthine; chiral phosphoric acid; cyclization; tryptamine