title: A short route toward chiral, polyhydroxylated indolizidines and quinolizidines.
abstract: In this paper, a rapid route toward functionalized bicyclic alkaloids is presented. In only three steps, an easily accessible carbohydrate derivative was converted into iodomethyl indolizidine 13, which can equilibrate to the corresponding iodoquinolizidine 15. We provide strong evidence that this equilibration proceeds via an aziridinium ion intermediate. Furthermore, nucleophilic substitution of the iodomethyl indolizidine as well as the aziridinium intermediate gives access to highly functionalized indolizidine and quinolizidine alkaloids.
authors.affiliation: Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
authors.forename: Steven H L
authors.initials: SH
authors.lastname: Verhelst
authors.forename: Baltasar
authors.initials: B
authors.lastname: Paez Martinez
authors.forename: Mattie S M
authors.initials: MS
authors.lastname: Timmer
authors.forename: Gerrit
authors.initials: G
authors.lastname: Lodder
authors.forename: Gijsbert A
authors.initials: GA
authors.lastname: van der Marel
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
authors.forename: Jacques H
authors.initials: JH
authors.lastname: van Boom
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D000478:Alkylation; D001388:Aziridines / Q000737:chemistry; D006900:Hydroxylation; D007212:Indolizines / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011807:Quinolizines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001388:Aziridines; D007212:Indolizines; D011807:Quinolizines