Synthesis of monoterpene piperidines from the iridoid glucoside antirrhinoside.

Henrik Franzyk, Signe Maria Frederiksen, Søren Rosendal Jensen

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    Synthesis of five novel piperidine monoterpene alkaloids using the iridoid glucoside antirrhinoside as a synthon is described. Two strategies for their preparation were investigated: the first possible pathway involved an intermediate diol from which the piperidine ring was expected to be constructed via reaction of its ditosylate with an amine; the second strategy involved a double reductive amination as the key step to the piperidine ring, which proved successful. The stereochemistry of C-5 and C-9 in the obtained piperidine monoterpenes was the same as that reported for alfa-Skytanthine, a known isolate from Skytanthus acutus (Apocynaceae).
    Original languageEnglish
    JournalJournal of Natural Products
    Pages (from-to)1012-1016
    Publication statusPublished - 1997

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