Synthesis of acetyl scopine. Intramolecular reactions of N-carbethoxy nortropine-3 alpha-benzenesulfenate
Апстракт
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.
Кључне речи:
6,7-dehydrotropine / scopine / tropine benzenesulfenate / intramolecular radical reactions / 1,5-hydrogen shiftИзвор:
Synlett, 1999, 5, 635-637Издавач:
- Georg Thieme Verlag, Stuttgart
DOI: 10.1055/s-1999-2658
ISSN: 0936-5214
WoS: 000080790200042
Scopus: 2-s2.0-0141894152
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Petrović, G. AU - Saičić, Radomir AU - Čeković, Živorad PY - 1999 UR - https://cherry.chem.bg.ac.rs/handle/123456789/415 AB - 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. PB - Georg Thieme Verlag, Stuttgart T2 - Synlett T1 - Synthesis of acetyl scopine. Intramolecular reactions of N-carbethoxy nortropine-3 alpha-benzenesulfenate IS - 5 SP - 635 EP - 637 DO - 10.1055/s-1999-2658 ER -
@article{ author = "Petrović, G. and Saičić, Radomir and Čeković, Živorad", year = "1999", abstract = "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.", publisher = "Georg Thieme Verlag, Stuttgart", journal = "Synlett", title = "Synthesis of acetyl scopine. Intramolecular reactions of N-carbethoxy nortropine-3 alpha-benzenesulfenate", number = "5", pages = "635-637", doi = "10.1055/s-1999-2658" }
Petrović, G., Saičić, R.,& Čeković, Ž.. (1999). Synthesis of acetyl scopine. Intramolecular reactions of N-carbethoxy nortropine-3 alpha-benzenesulfenate. in Synlett Georg Thieme Verlag, Stuttgart.(5), 635-637. https://doi.org/10.1055/s-1999-2658
Petrović G, Saičić R, Čeković Ž. Synthesis of acetyl scopine. Intramolecular reactions of N-carbethoxy nortropine-3 alpha-benzenesulfenate. in Synlett. 1999;(5):635-637. doi:10.1055/s-1999-2658 .
Petrović, G., Saičić, Radomir, Čeković, Živorad, "Synthesis of acetyl scopine. Intramolecular reactions of N-carbethoxy nortropine-3 alpha-benzenesulfenate" in Synlett, no. 5 (1999):635-637, https://doi.org/10.1055/s-1999-2658 . .