title: Biomimetic Approach toward the Total Synthesis of rac-2-(Acylmethylene)pyrrolidine Alkaloids.
abstract: 2-(Acylmethylene)pyrrolidine derivatives were synthesized via intermolecular decarbonylative Mannich reaction from various methyl ketones and 1-alkyl-1-pyrroliniums, generated in situ from 1-alkylprolines. This approach mimics the biosynthetic pathway and provides a direct access to a series of 2-(acylmethylene)pyrrolidine alkaloids, including hygrine, N-methylruspolinone, dehydrodarlinine, and ruspolinone.
authors.affiliation: Department of Chemistry, National Taiwan Normal University, Taipei 11677, Taiwan.
authors.forename: Yu-Chiao
authors.initials: YC
authors.lastname: Shih
authors.affiliation: Department of Chemistry, National Taiwan Normal University, Taipei 11677, Taiwan.
authors.forename: Pei-Hua
authors.initials: PH
authors.lastname: Tsai
authors.affiliation: Department of Chemistry, National Taiwan Normal University, Taipei 11677, Taiwan.
authors.forename: Chia-Chun
authors.initials: CC
authors.lastname: Hsu
authors.affiliation: Department of Chemistry, National Taiwan Normal University, Taipei 11677, Taiwan.
authors.forename: Chih-Wei
authors.initials: CW
authors.lastname: Chang
authors.affiliation: Department of Chemistry, National Taiwan Normal University, Taipei 11677, Taiwan.
authors.forename: Yuandong
authors.initials: Y
authors.lastname: Jhong
authors.affiliation: Department of Chemistry, National Taiwan Normal University, Taipei 11677, Taiwan.
authors.forename: Yun-Chung
authors.initials: YC
authors.lastname: Chen
authors.affiliation: Department of Chemistry, National Taiwan Normal University, Taipei 11677, Taiwan.
authors.forename: Tun-Cheng
authors.initials: TC
authors.lastname: Chien
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D032701:Biomimetics; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C000604891:2-(acylmethylene)pyrrolidine; D000470:Alkaloids; D011759:Pyrrolidines; C015946:hygrine; C032519:pyrrolidine