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dc.creatorBjelaković, Mira
dc.creatorKrstić, Natalija
dc.creatorTodorović, Nina
dc.creatorKrunić, A.
dc.creatorTinant, B.
dc.creatorDabović, Milan
dc.creatorPavlović, Vladimir D.
dc.date.accessioned2019-01-30T17:22:06Z
dc.date.available2019-01-30T17:22:06Z
dc.date.issued2009
dc.identifier.issn0040-4020
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/620
dc.description.abstractIn 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.publisherPergamon-Elsevier Science Ltd, Oxford
dc.relationinfo:eu-repo/grantAgreement/MESTD/MPN2006-2010/142033/RS//
dc.rightsrestrictedAccess
dc.sourceTetrahedron
dc.subject2D NMR spectroscopyen
dc.subject5a,14a-Dihydroxycholestan-3ß-yl acetateen
dc.subject5,10:13,14-Disecosteroidsen
dc.subjectHypoiodite reagenten
dc.subjectOxidative ß-fragmentationen
dc.title5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered ringsen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractКрунић, A.; Бјелаковић, Мира; Крстић, Наталија; Тодоровић, Нина; Тинант, Б.; Павловић, Владимир Д.; Дабовић, М.М.;
dc.citation.volume65
dc.citation.issue46
dc.citation.spage9557
dc.citation.epage9568
dc.citation.other65(46): 9557-9568
dc.citation.rankM21
dc.identifier.doi10.1016/j.tet.2009.09.066
dc.identifier.rcubConv_4221
dc.identifier.scopus2-s2.0-70349973061
dc.identifier.wos000271280400006
dc.type.versionpublishedVersion


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