A short route toward chiral, polyhydroxylated indolizidines and quinolizidines.
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.
Verhelst
Steven H L
SH
Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
Paez Martinez
Baltasar
B
Timmer
Mattie S M
MS
Lodder
Gerrit
G
van der Marel
Gijsbert A
GA
Overkleeft
Herman S
HS
van Boom
Jacques H
JH
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
D000470:Alkaloids; D001388:Aziridines; D007212:Indolizines; D011807:Quinolizines