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13,14-Seco-steroids: A New Type of Modified Steroids Containing a Nine-Membered Ring
dc.creator | Bjelaković, Mira | |
dc.creator | Lorenc, Ljubinka | |
dc.creator | Pavlović, Vladimir D. | |
dc.creator | Mihailović, Milhailo Lj. | |
dc.creator | Tinant, Bernard | |
dc.creator | Declercq, Jean-Paul | |
dc.creator | Kalvoda, Jaroslav | |
dc.date.accessioned | 2021-02-02T06:40:28Z | |
dc.date.available | 2021-02-02T06:40:28Z | |
dc.date.issued | 1999 | |
dc.identifier.issn | 0018-019X | |
dc.identifier.issn | 1522-2675 | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/4184 | |
dc.description.abstract | Oxidations of 14α‐hydroxy‐5α‐cholestan‐3β‐yl acetate (5) with lead tetraacetate under thermal or photolytic conditions or in the presence of iodine proceed mainly by fragmentation of the C(13)−C(14) bond to give as the primary products the 13,18‐didehydro‐13,14‐seco derivative 6 and the (E )‐Δ12‐13,14‐seco ketone 11, respectively. Further transformations of these compounds under conditions of their formation afforded, in addition, the acetoxy derivatives 7 – 9 (from 6), and the D‐homo‐C‐nor compound 12 and (12R,13R)‐epoxide 13 (from 11). Unexpectedly, the photolytic lead‐tetraacetate oxidation of 5 resulted partly (to ca. 20%) in a reversible fragmentation involving scission and recombination of the C(8)−C(14) bond followed by formation of the 14β,22‐ether 10. Possible mechanisms for the observed transformations are discussed. | |
dc.publisher | Wiley | en |
dc.rights | restrictedAccess | |
dc.source | Helvetica Chimica Acta | en |
dc.subject | Steroids | |
dc.subject | Oxidation | |
dc.subject | Lead-tetraacetate | |
dc.subject | photolytic conditions | |
dc.subject | thermal conditions | |
dc.title | 13,14-Seco-steroids: A New Type of Modified Steroids Containing a Nine-Membered Ring | en |
dc.type | article | en |
dc.rights.license | ARR | |
dcterms.abstract | Лоренц, Љубинка; Децлерцq, Јеан-Паул; Тинант, Бернард; Павловић, Владимир Д.; Калвода, Јарослав; Михаиловић, Михаило Љ.; Бјелаковић, Мира; | |
dc.citation.volume | 82 | |
dc.citation.issue | 5 | |
dc.citation.spage | 707 | |
dc.citation.epage | 721 | |
dc.identifier.doi | 10.1002/(SICI)1522-2675(19990505)82:5<707::AID-HLCA707>3.0.CO;2-O | |
dc.identifier.scopus | 2-s2.0-0032920731 | |
dc.type.version | publishedVersion |