TY  - JOUR
AU  - Petrović, GB
AU  - Saičić, Radomir
AU  - Čeković, Živorad
PY  - 2003
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/153
AB  - The synthesis of scopin acetate (6b) and 6,7-didehydrohyoscyamine (17) was achieved by using tropine (5) as the starting compound. Formal (phenylthio)-radical transfer to the nonactivated 6-position of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate (9) by irradiation in the presence of hexabutyldistannane is a key step of this synthetic approach, involving ethyl 6,7-didehydro-N-demethyltropine-N-carboxylate (15) as a synthetic intermediate (Schemes 3 and 5). The reaction of 9 with tributylstannane in the presence of ethyl acrylate, as a radicophilic olefin. involves Michael-type alkylation at C(6) of the tropine skeleton affording ethyl N-demethyl-N-(ethoxycarbonyl)tropine-6-propanoate (18) (Scheme 6).
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Helvetica Chimica Acta
T1  - Synthesis of scopin acetate and 6,7-didehydrohyoscyamin. Intramolecular phenylsulfenylation of a nonactivated methylene group of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate
VL  - 86
IS  - 9
SP  - 3179
EP  - 3186
DO  - 10.1002/hlca.200390258
ER  - 

@article{
author = "Petrović, GB and Saičić, Radomir and Čeković, Živorad",
year = "2003",
abstract = "The synthesis of scopin acetate (6b) and 6,7-didehydrohyoscyamine (17) was achieved by using tropine (5) as the starting compound. Formal (phenylthio)-radical transfer to the nonactivated 6-position of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate (9) by irradiation in the presence of hexabutyldistannane is a key step of this synthetic approach, involving ethyl 6,7-didehydro-N-demethyltropine-N-carboxylate (15) as a synthetic intermediate (Schemes 3 and 5). The reaction of 9 with tributylstannane in the presence of ethyl acrylate, as a radicophilic olefin. involves Michael-type alkylation at C(6) of the tropine skeleton affording ethyl N-demethyl-N-(ethoxycarbonyl)tropine-6-propanoate (18) (Scheme 6).",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Helvetica Chimica Acta",
title = "Synthesis of scopin acetate and 6,7-didehydrohyoscyamin. Intramolecular phenylsulfenylation of a nonactivated methylene group of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate",
volume = "86",
number = "9",
pages = "3179-3186",
doi = "10.1002/hlca.200390258"
}

Petrović, G., Saičić, R.,& Čeković, Ž.. (2003). Synthesis of scopin acetate and 6,7-didehydrohyoscyamin. Intramolecular phenylsulfenylation of a nonactivated methylene group of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate. in Helvetica Chimica Acta
Wiley-V C H Verlag Gmbh, Weinheim., 86(9), 3179-3186.
https://doi.org/10.1002/hlca.200390258

Petrović G, Saičić R, Čeković Ž. Synthesis of scopin acetate and 6,7-didehydrohyoscyamin. Intramolecular phenylsulfenylation of a nonactivated methylene group of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate. in Helvetica Chimica Acta. 2003;86(9):3179-3186.
doi:10.1002/hlca.200390258 .

Petrović, GB, Saičić, Radomir, Čeković, Živorad, "Synthesis of scopin acetate and 6,7-didehydrohyoscyamin. Intramolecular phenylsulfenylation of a nonactivated methylene group of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate" in Helvetica Chimica Acta, 86, no. 9 (2003):3179-3186,
https://doi.org/10.1002/hlca.200390258 . .