title: Expedient syntheses of antofine and cryptopleurine via intramolecular 1,3-dipolar cycloaddition.
abstract: The practical and expedient total syntheses of the representative phenanthroindolizidine and phenanthroquinolizidine alkaloids, antofine and cryptopleurine, are described. Construction of the pyrrolidine and piperidine ring of each alkaloid was achieved by using an intramolecular 1,3-dipolar cycloaddition of an azide onto an alkene and subsequent reduction of the resulting imine and aziridine.
authors.affiliation: College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea. pennkim@snu.ac.kr
authors.forename: Sanghee
authors.initials: S
authors.lastname: Kim
authors.forename: Yun Mi
authors.initials: YM
authors.lastname: Lee
authors.forename: Jaekwang
authors.initials: J
authors.lastname: Lee
authors.forename: Taeho
authors.initials: T
authors.lastname: Lee
authors.forename: Ye
authors.initials: Y
authors.lastname: Fu
authors.forename: Yanling
authors.initials: Y
authors.lastname: Song
authors.forename: Jihee
authors.initials: J
authors.lastname: Cho
authors.forename: Deukjoon
authors.initials: D
authors.lastname: Kim
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D015394:Molecular Structure; D010618:Phenanthrolines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000470:Alkaloids; D006571:Heterocyclic Compounds; D007211:Indoles; D010618:Phenanthrolines; C473343:antofine; C007160:cryptopleurine