Приказ основних података о документу
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
dc.creator | Petrović, GB | |
dc.creator | Saičić, Radomir | |
dc.creator | Čeković, Živorad | |
dc.date.accessioned | 2018-11-22T00:05:35Z | |
dc.date.available | 2018-11-22T00:05:35Z | |
dc.date.issued | 2003 | |
dc.identifier.issn | 0018-019X | |
dc.identifier.uri | https://cherry.chem.bg.ac.rs/handle/123456789/153 | |
dc.description.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). | en |
dc.publisher | Wiley-V C H Verlag Gmbh, Weinheim | |
dc.rights | restrictedAccess | |
dc.source | Helvetica Chimica Acta | |
dc.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 | en |
dc.type | article | |
dc.rights.license | ARR | |
dc.citation.volume | 86 | |
dc.citation.issue | 9 | |
dc.citation.spage | 3179 | |
dc.citation.epage | 3186 | |
dc.identifier.wos | 000185730000016 | |
dc.identifier.doi | 10.1002/hlca.200390258 | |
dc.citation.other | 86(9): 3179-3186 | |
dc.citation.rank | M21 | |
dc.type.version | publishedVersion | en |
dc.identifier.scopus | 2-s2.0-0141955010 |