5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings
Samo za registrovane korisnike
2009
Autori
Bjelaković, Mira
Krstić, Natalija

Todorović, Nina

Krunić, Aleksej
Tinant, Bernard
Dabović, Milan
Pavlović, Vladimir D.
Članak u časopisu (Objavljena verzija)

Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
2D NMR spectroscopy / 5a,14a-Dihydroxycholestan-3ß-yl acetate / 5,10:13,14-Disecosteroids / Hypoiodite reagent / Oxidative ß-fragmentationIzvor:
Tetrahedron, 2009, 65, 46, 9557-9568Izdavač:
- Oxford : Pergamon-Elsevier Science Ltd
Finansiranje / projekti:
DOI: 10.1016/j.tet.2009.09.066
ISSN: 0040-4020
WoS: 000271280400006
Scopus: 2-s2.0-70349973061
Institucija/grupa
IHTMTY - JOUR AU - Bjelaković, Mira AU - Krstić, Natalija AU - Todorović, Nina AU - Krunić, Aleksej AU - Tinant, Bernard AU - Dabović, Milan AU - Pavlović, Vladimir D. PY - 2009 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/620 AB - 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. PB - Oxford : Pergamon-Elsevier Science Ltd T2 - Tetrahedron T1 - 5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings VL - 65 IS - 46 SP - 9557 EP - 9568 DO - 10.1016/j.tet.2009.09.066 ER -
@article{ author = "Bjelaković, Mira and Krstić, Natalija and Todorović, Nina and Krunić, Aleksej and Tinant, Bernard and Dabović, Milan and Pavlović, Vladimir D.", year = "2009", 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.", publisher = "Oxford : Pergamon-Elsevier Science Ltd", journal = "Tetrahedron", title = "5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings", volume = "65", number = "46", pages = "9557-9568", doi = "10.1016/j.tet.2009.09.066" }
Bjelaković, M., Krstić, N., Todorović, N., Krunić, A., Tinant, B., Dabović, M.,& Pavlović, V. D.. (2009). 5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings. in Tetrahedron Oxford : Pergamon-Elsevier Science Ltd., 65(46), 9557-9568. https://doi.org/10.1016/j.tet.2009.09.066
Bjelaković M, Krstić N, Todorović N, Krunić A, Tinant B, Dabović M, Pavlović VD. 5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings. in Tetrahedron. 2009;65(46):9557-9568. doi:10.1016/j.tet.2009.09.066 .
Bjelaković, Mira, Krstić, Natalija, Todorović, Nina, Krunić, Aleksej, Tinant, Bernard, Dabović, Milan, Pavlović, Vladimir D., "5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings" in Tetrahedron, 65, no. 46 (2009):9557-9568, https://doi.org/10.1016/j.tet.2009.09.066 . .