Synthesis of carbocyclic homo-N-nucleosides from iridoids

Henrik Franzyk, Jon Holbech Rasmussen, Rafaele Antonio Mazzei, Søren Rosendal Jensen

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    Two iridoid glucosides, antirrhinoside (1) and catalpol (2), were converted into selectively protected polysubstituted cyclopentylmethanols, which were subsequently used to prepare carbocyclic homo-N-nucleosides (5, 6 and 14). A purine moiety was introduced either by the Mitsunobu reaction or by substitution of a primary triflate with the tetrabutylammonium salt of 6-iodopurine. The latter method was superior with regard to both ease of purification and yield. The N-9 vs. N-7 regioselectivity of the salts of different 6-substituted purine derivatives was briefly investigated.
    Original languageEnglish
    JournalEuropean Journal of Organic Chemistry
    Issue number12
    Pages (from-to)2931-2935
    Publication statusPublished - 1998

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