Conversion of the Iridoid Glucoside Antirrhinoside into 3-Azabicyclo[3.3.0]-octane Building Blocks

Henrik Franzyk, Signe Maria Frederiksen, Søren Rosendal Jensen

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    The iridoid glucoside antirrhinoside (1) was transformed into polysubstituted 3-azabicyclo[3.3.0]octanes 3, 12 and 13 in 4-5 steps. Ozonolysis of the diacetonide of 1 and of its 7-deoxy-derivative 8 afforded cyclopentanoids 2 and 10, respectively. Conditions for the selective conversion of 2 and 10 into the corresponding ditosylates 4 and 11 were investigated. Cyclization of 4 and 11 was achieved with benzylamine and 2-methoxybenzylamine to yield bicyclic pyrrolidines 3, 12 and 13. Additional building blocks 14 and 15 were obtained by selective deprotection of the N-benzyl and isopropylidene moieties in 12 and 13, respectively
    Original languageEnglish
    JournalJournal of Natural Products
    Issue number5
    Pages (from-to)592-595
    Publication statusPublished - 2000

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