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Oksidativne fragmentacije 5-hidroksi-1-okso-5α-holestan-3β-il-acetata

dc.creatorKrstić, Natalija
dc.creatorBjelaković, Mira
dc.creatorLorenc, Ljubinka
dc.creatorPavlović, Vladimir D.
dc.date.accessioned2019-01-30T17:11:13Z
dc.date.available2019-01-30T17:11:13Z
dc.date.issued2003
dc.identifier.issn0352-5139
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/109
dc.description.abstract5-hydroxy-1-oxo-5α-cholestan-3β-yl acetate (11) was prepared in 5 steps starting from (E)-3β-acetoxy-5,10-seco-1(10)-cholesten-5-one (6). Treatment of the 1-oxo-5-hydroxy derivative 11 with lead tetraacetate (LTA) (under thermal or hypoiodite conditions) or with mercuric oxide/iodine (HgO/I2) reagent resulted in the oxidative β-fragmentation of the C(5)–C(10) bond affording 1,5-dioxo-5,10-secocholest-10(19)-en-3β-yl acetate (12), in different yields, depending on the reagent. Also the stereochemistry of the 1β,6β-cyclization product 13, formed by transannular cyclization of the 1,5-diketone 12 on silica gel, is discussed in this work.en
dc.description.abstractSintetizovan je 5-hidroksi-1-okso-5α-holestan-3β-il-acetata (11) u 5 faza polazeći od (E)- 3β-acetoksi-5,10-seko-1(10)-holesten-5-ona (6). Dejstvom olovo-tetraacetata (LTA) (pod termičkim ili hipojoditnim uslovima), ili merkuri-oksid/jodnog reagensa (HgO/I2) na 1-okso-5-hidroksi derivat 11, vrši se oksidativna β-fragmentacija njegove C(5)–C(10) veze, pri čemu se dobija 1,5-diokso-5,10-sekoholest-10(19)-en-3β-il-acetat (12), u različitim prinosima u zavisnosti od upotrebljenog reagensa. Takođe, diskutovana je stereohemija 1β,6β-ciklizacionog proizvoda 13, nastalog intramolekulskom ciklizacijom 1,5-diokso-5,10-seko jedinjenja 12 na silika gelu.sr
dc.publisherSerbian Chemical Society
dc.relationProject MESTD, br. 1702: Synthesis and chemical transformations of steroidal and modified steroidal molecules
dc.rightsopenAccess
dc.sourceJournal of the Serbian Chemical Society
dc.subject5-Hydroxy-1-oxo-5α-cholestan-3β-yl acetateen
dc.subject1,5-dioxo-5,10-secocholest-10(19)-en-3β-yl acetateen
dc.subjectβ-fragmentationen
dc.subjecttransannular cyclizationen
dc.titleOxidative fragmentation of 5-hydroxy-1-oxo-5α-cholestan-3β-yl acetateen
dc.titleOksidativne fragmentacije 5-hidroksi-1-okso-5α-holestan-3β-il-acetatasr
dc.typearticle
dc.rights.licenseBY-NC-ND
dcterms.abstractКрстић, Наталија; Лоренц, Љубинка Б.; Бјелаковић, Мира; Павловић, Владимир Д.; Оксидативне фрагментације 5-хидрокси-1-оксо-5α-холестан-3β-ил-ацетата; Оксидативне фрагментације 5-хидрокси-1-оксо-5α-холестан-3β-ил-ацетата;
dc.citation.volume68
dc.citation.issue11
dc.citation.spage785
dc.citation.epage794
dc.citation.other68(11): 785-794
dc.citation.rankM23
dc.identifier.doi10.2298/JSC0311785K
dc.identifier.rcubConv_177
dc.identifier.fulltexthttp://cer.ihtm.bg.ac.rs//bitstream/id/7635/107.pdf
dc.identifier.scopus2-s2.0-1442310833
dc.type.versionpublishedVersion


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