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dc.creatorPetrović, GB
dc.creatorSaičić, Radomir
dc.creatorČeković, Živorad
dc.date.accessioned2018-11-22T00:05:35Z
dc.date.available2018-11-22T00:05:35Z
dc.date.issued2003
dc.identifier.issn0018-019X
dc.identifier.urihttps://cherry.chem.bg.ac.rs/handle/123456789/153
dc.description.abstractThe 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.publisherWiley-V C H Verlag Gmbh, Weinheim
dc.rightsrestrictedAccess
dc.sourceHelvetica Chimica Acta
dc.titleSynthesis of scopin acetate and 6,7-didehydrohyoscyamin. Intramolecular phenylsulfenylation of a nonactivated methylene group of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylateen
dc.typearticle
dc.rights.licenseARR
dc.citation.volume86
dc.citation.issue9
dc.citation.spage3179
dc.citation.epage3186
dc.identifier.wos000185730000016
dc.identifier.doi10.1002/hlca.200390258
dc.citation.other86(9): 3179-3186
dc.citation.rankM21
dc.type.versionpublishedVersionen
dc.identifier.scopus2-s2.0-0141955010


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Приказ основних података о документу