dc.creator | Mihailović, Milhailo Lj. | |
dc.creator | Dabović, Milan | |
dc.creator | Pavlović, Vladimir D. | |
dc.creator | Krstić, Natalija | |
dc.creator | Lorenc, Ljubinka | |
dc.date.accessioned | 2019-04-26T15:09:21Z | |
dc.date.available | 2019-04-26T15:09:21Z | |
dc.date.issued | 1997 | |
dc.identifier.issn | 0352-5139 | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/2707 | |
dc.description.abstract | 5-Hydroxy-5α-cholest-8-en-3β-yl acetate (8) (prepared in 6 steps starting from 7-dehydrocholesteryl acetate (1) was transformed with ruthenium tetroxide to 5-hydroxy-8,9-dioxo-8,9-seco-5α-cholestan-3β-yl acetate (9). Treatment of the latter 8,9-seco-5-hydroxy derivative with lead tetraacetate (LTA) or mercuric oxide/iodine reagent (HgO/I2) resulted, instead of the expected oxidative β-fragmentation of its C(5)-C(10) bond, in the competing non-regio and non-stereoselective acetoxylation of the α-positions next to the 8- and 9-oxo functions (with LTA), and in the ≈ 82% recovery of the starting material (with HgO/I2). The results are discussed in terms of the strong hydrogen bonding which exists between the 5α-hydroxyl and the 8-oxo group. | en |
dc.publisher | Serbian Chemical Society | |
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 | Lactones | |
dc.subject | Acetates | |
dc.subject | secosteroidal macrocycles | |
dc.title | Synthesis and oxidative transformations of 5-hydroxy-5α-cholest-8-en-3β-yl acetate | en |
dc.type | article | en |
dc.rights.license | BY-NC-ND | |
dcterms.abstract | Михаиловић, М. Љ.; Лоренц, Љубинка; Крстић, Н М; Дабовић, М.; Павловић, В Д; | |
dc.citation.volume | 62 | |
dc.citation.issue | 9 | |
dc.citation.spage | 719 | |
dc.citation.epage | 726 | |
dc.identifier.rcub | https://hdl.handle.net/21.15107/rcub_cer_2707 | |
dc.identifier.scopus | 2-s2.0-0038979692 | |
dc.type.version | publishedVersion | |