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Kiselo-katalizovana i fotolitička reaktivnost nekih nezasićenih B-nor-5,10-sekosteroidnih ketona

dc.creatorBjelaković, Mira
dc.creatorPavlović, Vladimir D.
dc.creatorDabović, Milan
dc.creatorLorenc, Ljubinka
dc.date.accessioned2019-01-30T17:11:24Z
dc.date.available2019-01-30T17:11:24Z
dc.date.issued2003
dc.identifier.issn0352-5139
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/115
dc.description.abstractThe acid-catalyzed reaction of (Z)- and (E)-B-nor-5,10-seco-ketones 2 and 3 resulted in an intramolecular cyclization to give the 5-hydroxy-A-nor-1β,5β-10(19)-methylidene derivative 8, the 5β-hydroxy-A-nor-1(10)-unsaturated compound 9 and the 5β,10β-dihydroxy A-nor-product 10, from the (Z)-isomer and the 5-hydroxy-A-nor-1β,5β-10(19)-methylidene product 11, from the (E)-isomer. Upon UV-irradiation, the (Z)- and (E)-seco-ketones 2 and 3 underwent a reversible (Z)/(E) and (E)/(Z)-isomerization and in addition to a transannular photocyclization to afford the 10(19)-methylidene derivatives 8 and 11, respectively, while photolysis of the 10(19)-methylidene-B-nor-5,10-seco-ketone 4 gave the oxetane derivative 12.en
dc.description.abstractKiselo-katalizovana reakcija (Z)- i (E)-B-nor-5,10-seko-ketona 2 i 3 rezultuje u intramolekulskoj ciklizaciji dajući 5-hidroksi-A-nor-1β,5β-10(19)-metilidenski derivat 8, 5β-hidroksi A-nor-1(10)-nezasićeno jedinjenje 9 i 5β,10β-dihidroksi-A-nor-proizvod 10, iz Z-izomera, i 5-hidroksi-A-nor-1β,5β-10(19)-metilidenski proizvod 11, iz E-izomera. (Z)- i (E)-Seko- ketoni 2 i 3 UV-ozračivanjem podležu reverzibilnoj (Z)/(E) odnosno (E)/(Z) izomerizaciji, kao i transanularnoj fotociklizaciji dajući 10(19)-metilidenske derivate 8 odnosno 11, dok se fotolizom 10(19)-metilidenskog-5,10-seko-ketona 4 gradi oksetanski derivat 12.sr
dc.publisherSerbian Chemical Society
dc.rightsopenAccess
dc.sourceJournal of the Serbian Chemical Society
dc.subject(Z)- and (E)-B-nor-5,10-secosteroidal ketonesen
dc.subject10(19)-methylidene-B-nor-5,10-secosteroidal ketoneen
dc.subjectacid-catalyzed reactionsen
dc.subjectphotolytic reactionsen
dc.subjectmechanistic interpretationen
dc.titleAcid-catalyzed and photolytic reactivity of some unsaturated B-nor-5, 10-secosteroidal ketonesen
dc.titleKiselo-katalizovana i fotolitička reaktivnost nekih nezasićenih B-nor-5,10-sekosteroidnih ketonasr
dc.typearticle
dc.rights.licenseBY-NC-ND
dcterms.abstractБјелаковић, Мира; Лоренц, Љубинка Б.; Дабовић, Милан М.; Павловић, Владимир Д.; Кисело-катализована и фотолитичка реактивност неких незасићених Б-нор-5,10-секостероидних кетона; Кисело-катализована и фотолитичка реактивност неких незасићених Б-нор-5,10-секостероидних кетона;
dc.citation.volume68
dc.citation.issue4-5
dc.citation.spage303
dc.citation.epage312
dc.citation.other68(4-5): 303-312
dc.citation.rankM23
dc.identifier.doi10.2298/JSC0305303B
dc.identifier.rcubConv_170
dc.identifier.fulltexthttp://cer.ihtm.bg.ac.rs//bitstream/id/7679/113.pdf
dc.identifier.scopus2-s2.0-0037835592
dc.type.versionpublishedVersion


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