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Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids
dc.creator | Bjelaković, Mira | |
dc.creator | Krstić, Natalija | |
dc.creator | Milić, Dragana | |
dc.creator | Kop, Tatjana | |
dc.creator | Robeyns, Koen | |
dc.creator | Pavlović, Vladimir D. | |
dc.date.accessioned | 2019-01-30T17:32:50Z | |
dc.date.available | 2019-01-30T17:32:50Z | |
dc.date.issued | 2012 | |
dc.identifier.issn | 0040-4020 | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/1114 | |
dc.description.abstract | The present study is concerned with the oxidative behaviour of unsaturated and epoxy 5-oxo-5,10-secosteroids in the presence of m-CPBA or TFAA-UHP as oxidants in order to investigate potential parameters controlling the chemoselectivity and regioselectivity. In the study we discovered a striking difference in the chemical behaviour of stereoisomeric compounds, (Z)- and (E)-3 beta-acetoxy-5,10-secocholest-1(10)-en-5-ones, as well as 1S,10R- and 1R,10R-epoxides. The secoketones were oxidized with exclusively C-6 migration and Baeyer-Villiger rearrangement product formation, whereas their stereoisomers provided the ring-contracted products, without lactone formation. The preferred conformation of expanded and contracted rings was established by NOESY correlations. The structures of two obtained lactones were also confirmed by X-ray analysis. The mechanistic and stereochemical aspects of these transformations are discussed. | en |
dc.publisher | Oxford : Pergamon-Elsevier Science Ltd | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172002/RS// | |
dc.rights | restrictedAccess | |
dc.source | Tetrahedron | |
dc.subject | 5-Oxo-5,10-secosteroids | en |
dc.subject | 5,10-Secosteroidal 5,6-lactones | en |
dc.subject | m-CPBA | en |
dc.subject | TFAA-UHP reagent | en |
dc.subject | Baeyer-Villiger oxidation | en |
dc.title | Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Бјелаковић, Мира; Коп, Татјана; Милиц, Драгана Р.; Павловиц, Владимир Д.; Крстић, Наталија; Робеyнс, Коен; | |
dc.citation.volume | 68 | |
dc.citation.issue | 36 | |
dc.citation.spage | 7479 | |
dc.citation.epage | 7488 | |
dc.citation.other | 68(36): 7479-7488 | |
dc.citation.rank | M22 | |
dc.identifier.doi | 10.1016/j.tet.2012.06.024 | |
dc.identifier.scopus | 2-s2.0-84864279987 | |
dc.identifier.wos | 000307698100029 | |
dc.type.version | publishedVersion |