Synthesis of acetyl scopine. Intramolecular reactions of N-carbethoxy nortropine-3 alpha-benzenesulfenate
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The synthesis of acetyl scopine using tropine as a starting compound was achieved. Free radical phenylthio group transfer to the 6-position, in the reaction of N-carbethoxy nortropine-3 alpha-benzenesulfenate with hexabutylditin, is a key step of this synthetic approach to scopine. The reaction of N-carbethoxy nortropine-benzenesulfenate with tributyltin hydride in the presence of a radicophilic olefin involves Michael type alkylation at the 6-position of tropine skeleton affording 6-(2-carbethoxyethyl)-N-carbethoxy nortropine in 31% yield.
Keywords:6,7-dehydrotropine / scopine / tropine benzenesulfenate / intramolecular radical reactions / 1,5-hydrogen shift
Source:Synlett, 1999, 5, 635-637
- Georg Thieme Verlag, Stuttgart