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
Само за регистроване кориснике
2003
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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).
Извор:
Helvetica Chimica Acta, 2003, 86, 9, 3179-3186Издавач:
- Wiley-V C H Verlag Gmbh, Weinheim
DOI: 10.1002/hlca.200390258
ISSN: 0018-019X
WoS: 000185730000016
Scopus: 2-s2.0-0141955010
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - 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 . .