A short route toward chiral, polyhydroxylated indolizidines and quinolizidines |
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Authors: | Verhelst Steven H L Paez Martinez Baltasar Timmer Mattie S M Lodder Gerrit van der Marel Gijsbert A Overkleeft Herman S van Boom Jacques H |
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Institution: | Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands. |
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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. |
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