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Synlett 1999; 1999(5): 635-637
DOI: 10.1055/s-1999-2658
DOI: 10.1055/s-1999-2658
letter
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Synthesis of Acetyl Scopine. Intramolecular Reactions of N-Carbethoxy Nortropine-3α-benzenesulfenate
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Publikationsverlauf
Publikationsdatum:
31. Dezember 1999 (online)
![](https://www.thieme-connect.de/media/synlett/199905/lookinside/thumbnails/10.1055-s-1999-2658-1.jpg)
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