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Synlett 1999; 1999(5): 635-637
DOI: 10.1055/s-1999-2658
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Synthesis of Acetyl Scopine. Intramolecular Reactions of N-Carbethoxy Nortropine-3α-benzenesulfenate

Goran Petrović* , Radomir N. Saičić, živorad Čeković
  • *Faculty of Chemistry, University of Belgrade, Studentski trg 16, PO Box 158, 11000 Belgrade, Yugoslavia; Fax +3 81-11-6 36-0 61; E-mail: zcekovic@chem.bg.ac.yu
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Publication Date:
31 December 1999 (online)

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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-α-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.

6,7-dehydrotropine - scopine - tropine benzenesulfenate - intramolecular radical reactions - 1,5-hydrogen shift