title: Synthesis of the tricyclic core in stemonamine alkaloids via one-pot gold(I)-catalyzed cyclization and schmidt rearrangement: formal synthesis of (±)-stemonamine.
abstract: An efficient synthesis of the tricyclic cyclopenta[1,2-b]pyrrolo[1,2-a]azepine nucleus of stemonamine alkaloids is reported. The key reaction utilizes a one-pot gold(I)-catalyzed cyclization and SnCl4-mediated Schmidt rearrangement. Notably, the phosphine ligand had a crucial effect on the gold(I)-catalyzed cyclization. As an application of this new methodology, the formal synthesis of (±)-stemonamine has been accomplished.
authors.affiliation: Department of Chemistry, POSTECH , 77 Cheongam-Ro, Nam-Gu, Pohang, Kyungbuk, Republic of Korea , 790-784.
authors.forename: Cheoljae
authors.initials: C
authors.lastname: Kim
authors.forename: Soyeong
authors.initials: S
authors.lastname: Kang
authors.forename: Young Ho
authors.initials: YH
authors.lastname: Rhee
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001381:Azepines; D006575:Heterocyclic Compounds, 3-Ring; C530508:stemonamine; D006046:Gold; D015107:4-Butyrolactone