title: Total synthesis of (+/-)-monomorine I and (+/-)-indolizidine 195B by an aza-[2,3]-Wittig rearrangement of a vinylaziridine.
abstract: A novel synthesis of (+/-)-monomorine I (1) and (+/-)-indolizidine 195B (2) is described in which the key step is the highly efficient aza-[2,3]-Wittig rearrangement of vinylaziridine 12 into tetrahydropyridine 13. Functional group manipulation then gave ketone 16 which could be converted into the target alkaloids by reductive amination (1:2 1.5:1).
authors.affiliation: Organic Chemistry 2, Lund Institute of Technology, Lund University, Sweden.
authors.forename: P
authors.initials: P
authors.lastname: Somfai
authors.forename: T
authors.initials: T
authors.lastname: Jarevång
authors.forename: U M
authors.initials: UM
authors.lastname: Lindström
authors.forename: A
authors.initials: A
authors.lastname: Svensson
mesh_terms: D000818:Animals; D001372:Aza Compounds / Q000737:chemistry; D007212:Indolizines / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy
chemical_list: D001372:Aza Compounds; D007212:Indolizines; C110223:indolizidine-195B