title: Total synthesis of (-)-kaitocephalin based on a Rh-catalyzed C-H amination.
abstract: A total synthesis of (-)-kaitocephalin, an ionotropic glutamate receptor antagonist, is accomplished in highly stereocontrolled manner via Overman rearrangement, rhodium-catalyzed benzylic C-H amination, pyrrolidine formation involving nucleophilic opening of a cyclic sulfamate, and rhodium-catalyzed allylic C-H amination as key steps.
authors.affiliation: Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki, 852-8521, Japan.
authors.forename: Keisuke
authors.initials: K
authors.lastname: Takahashi
authors.forename: Daisuke
authors.initials: D
authors.lastname: Yamaguchi
authors.forename: Jun
authors.initials: J
authors.lastname: Ishihara
authors.forename: Susumi
authors.initials: S
authors.lastname: Hatakeyama
mesh_terms: D000586:Amination; D002384:Catalysis; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D013451:Sulfonic Acids
chemical_list: D011758:Pyrroles; D013451:Sulfonic Acids; C442421:kaitocephalin; C005741:sulfamic acid; D012238:Rhodium