title: Asymmetric total synthesis of Apocynaceae hydrocarbazole alkaloids (+)-deethylibophyllidine and (+)-limaspermidine.
abstract: An unprecedented asymmetric catalytic tandem aminolysis/aza-Michael addition reaction of spirocyclic para-dienoneimides has been designed and developed through organocatalytic enantioselective desymmetrization. A unified strategy based on this key tandem methodology has been divergently explored for the asymmetric total synthesis of two natural Apocynaceae alkaloids, (+)-deethylibophyllidine and (+)-limaspermidine. The present studies not only enrich the tandem reaction design concerning the asymmetric catalytic assembly of a chiral all-carbon quaternary stereocenter contained in the densely functionalized hydrocarbazole synthons but also manifest the potential for the application of the asymmetric catalysis based on the para-dienone chemistry in asymmetric synthesis of natural products.
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000, China.
authors.forename: Ji-Yuan
authors.initials: JY
authors.lastname: Du
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000, China.
authors.forename: Chao
authors.initials: C
authors.lastname: Zeng
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000, China.
authors.forename: Xiao-Jie
authors.initials: XJ
authors.lastname: Han
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000, China.
authors.forename: Hu
authors.initials: H
authors.lastname: Qu
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000, China.
authors.forename: Xian-He
authors.initials: XH
authors.lastname: Zhao
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000, China.
authors.forename: Xian-Tao
authors.initials: XT
authors.lastname: An
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000, China.|‡Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China.
authors.forename: Chun-An
authors.initials: CA
authors.lastname: Fan
mesh_terms: D029062:Apocynaceae / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D002227:Carbazoles; D026121:Indole Alkaloids; C579383:limaspermidine