dc.creator | Bjelaković, Mira | |
dc.creator | Krstić, Natalija | |
dc.creator | Todorović, Nina | |
dc.creator | Krunić, Aleksej | |
dc.creator | Tinant, Bernard | |
dc.creator | Dabović, Milan | |
dc.creator | Pavlović, Vladimir D. | |
dc.date.accessioned | 2019-01-30T17:22:06Z | |
dc.date.available | 2019-01-30T17:22:06Z | |
dc.date.issued | 2009 | |
dc.identifier.issn | 0040-4020 | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/620 | |
dc.description.abstract | In this paper a synthetic pathway to the modified 5,10:13,14-bisfragmentation cholestane derivatives 8-14 is described. The synthesis involves introduction of the 5α- and 14α-hydroxyl groups in the cholestane molecule and subsequent cleavage of the C(5)-C(10) bond in 5α,14α-dihydroxycholestan-3β-yl acetate (4) with the HgO/I2 reagent and the C(13)-C(14) bond in the stereoisomeric 14α-hydroxy-5,10-secosteroids 5 and 6 with the Pb(OAc)4/I2 reagent. Complete and unambiguous 1H and 13C NMR resonance assignments of the obtained secosteroids, as well as the solution conformations of their 10- and 9-membered rings were determined by extensive analysis of 1D and 2D NMR spectral data. The structures and the solid-state conformations of 5,10-secosteroids 5-7 were confirmed by X-ray analysis. All diseco-compounds have a novel 5,10:13,14-disecocholestane skeleton. | en |
dc.publisher | Oxford : Pergamon-Elsevier Science Ltd | |
dc.relation | info:eu-repo/grantAgreement/MESTD/MPN2006-2010/142033/RS// | |
dc.rights | restrictedAccess | |
dc.source | Tetrahedron | |
dc.subject | 2D NMR spectroscopy | en |
dc.subject | 5a,14a-Dihydroxycholestan-3ß-yl acetate | en |
dc.subject | 5,10:13,14-Disecosteroids | en |
dc.subject | Hypoiodite reagent | en |
dc.subject | Oxidative ß-fragmentation | en |
dc.title | 5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Крунић, A.; Бјелаковић, Мира; Крстић, Наталија; Тодоровић, Нина; Тинант, Б.; Павловић, Владимир Д.; Дабовић, М.М.; | |
dc.citation.volume | 65 | |
dc.citation.issue | 46 | |
dc.citation.spage | 9557 | |
dc.citation.epage | 9568 | |
dc.citation.other | 65(46): 9557-9568 | |
dc.citation.rank | M21 | |
dc.identifier.doi | 10.1016/j.tet.2009.09.066 | |
dc.identifier.scopus | 2-s2.0-70349973061 | |
dc.identifier.wos | 000271280400006 | |
dc.type.version | publishedVersion | |