Приказ основних података о документу
Oxidative fragmentation of 5-hydroxy-1-oxo-5α-cholestan-3β-yl acetate
Oksidativne fragmentacije 5-hidroksi-1-okso-5α-holestan-3β-il-acetata
dc.creator | Krstić, Natalija | |
dc.creator | Bjelaković, Mira | |
dc.creator | Lorenc, Ljubinka | |
dc.creator | Pavlović, Vladimir D. | |
dc.date.accessioned | 2019-01-30T17:11:13Z | |
dc.date.available | 2019-01-30T17:11:13Z | |
dc.date.issued | 2003 | |
dc.identifier.issn | 0352-5139 | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/109 | |
dc.description.abstract | 5-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.abstract | Sintetizovan 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.publisher | Serbian Chemical Society | |
dc.relation | Project MESTD, br. 1702: Synthesis and chemical transformations of steroidal and modified steroidal molecules | |
dc.rights | openAccess | |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/4.0/ | |
dc.source | Journal of the Serbian Chemical Society | |
dc.subject | 5-Hydroxy-1-oxo-5α-cholestan-3β-yl acetate | en |
dc.subject | 1,5-dioxo-5,10-secocholest-10(19)-en-3β-yl acetate | en |
dc.subject | β-fragmentation | en |
dc.subject | transannular cyclization | en |
dc.title | Oxidative fragmentation of 5-hydroxy-1-oxo-5α-cholestan-3β-yl acetate | en |
dc.title | Oksidativne fragmentacije 5-hidroksi-1-okso-5α-holestan-3β-il-acetata | sr |
dc.type | article | |
dc.rights.license | BY-NC-ND | |
dcterms.abstract | Крстић, 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.volume | 68 | |
dc.citation.issue | 11 | |
dc.citation.spage | 785 | |
dc.citation.epage | 794 | |
dc.citation.other | 68(11): 785-794 | |
dc.citation.rank | M23 | |
dc.identifier.doi | 10.2298/JSC0311785K | |
dc.identifier.fulltext | https://cer.ihtm.bg.ac.rs//bitstream/id/7635/107.pdf | |
dc.identifier.scopus | 2-s2.0-1442310833 | |
dc.identifier.wos | 000187394400001 | |
dc.type.version | publishedVersion |