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Synthesis and oxidative transformations of 5-hydroxy-5α-cholest-8-en-3β-yl acetate

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Authors
Mihailović, Milhailo Lj.
Dabović, Milan
Pavlović, Vladimir D.
Krstić, Natalija
Lorenc, Ljubinka
Article (Published version)
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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.
Keywords:
Lactones / Acetates / secosteroidal macrocycles
Source:
Journal of the Serbian Chemical Society, 1997, 62, 9, 719-726
Publisher:
  • Serbian Chemical Society

ISSN: 0352-5139

Scopus: 2-s2.0-0038979692
[ Google Scholar ]
2
Handle
https://hdl.handle.net/21.15107/rcub_cer_2707
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/2707
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Dabović, Milan
AU  - Pavlović, Vladimir D.
AU  - Krstić, Natalija
AU  - Lorenc, Ljubinka
PY  - 1997
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2707
AB  - 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.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis and oxidative transformations of 5-hydroxy-5α-cholest-8-en-3β-yl acetate
VL  - 62
IS  - 9
SP  - 719
EP  - 726
UR  - https://hdl.handle.net/21.15107/rcub_cer_2707
ER  - 
@article{
author = "Mihailović, Milhailo Lj. and Dabović, Milan and Pavlović, Vladimir D. and Krstić, Natalija and Lorenc, Ljubinka",
year = "1997",
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.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis and oxidative transformations of 5-hydroxy-5α-cholest-8-en-3β-yl acetate",
volume = "62",
number = "9",
pages = "719-726",
url = "https://hdl.handle.net/21.15107/rcub_cer_2707"
}
Mihailović, M. Lj., Dabović, M., Pavlović, V. D., Krstić, N.,& Lorenc, L.. (1997). Synthesis and oxidative transformations of 5-hydroxy-5α-cholest-8-en-3β-yl acetate. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 62(9), 719-726.
https://hdl.handle.net/21.15107/rcub_cer_2707
Mihailović ML, Dabović M, Pavlović VD, Krstić N, Lorenc L. Synthesis and oxidative transformations of 5-hydroxy-5α-cholest-8-en-3β-yl acetate. in Journal of the Serbian Chemical Society. 1997;62(9):719-726.
https://hdl.handle.net/21.15107/rcub_cer_2707 .
Mihailović, Milhailo Lj., Dabović, Milan, Pavlović, Vladimir D., Krstić, Natalija, Lorenc, Ljubinka, "Synthesis and oxidative transformations of 5-hydroxy-5α-cholest-8-en-3β-yl acetate" in Journal of the Serbian Chemical Society, 62, no. 9 (1997):719-726,
https://hdl.handle.net/21.15107/rcub_cer_2707 .

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