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Stereoselective transformation of cyclodecene-1,4-dione systems, derived from steroids, to the corresponding spiro-g-lactones. A semiempirical MO Study
The thermal and acid-catalyzed intramolecular rearrangement of the (Z)- and (E)-cyclodecene-1,4-dione compounds deriving from steroids, 2a,b and 3a,b, respectively, proceeds stereoselectively to give the corresponding configurationally different spiro-γ-lactone derivatives, the (5R,9R)-isomers 4a,b (from the (Z)-cyclodecenediones 2a,b) and the (5R,9S)-isomers 5a,b (from the (E)-cyclodecenediones 3a,b). The semiempirical MNDOAM1 and PM3 molecular orbital methods were applied to elucidate the possible mechanistic pathway of the observed intramolecular process leading to the spiro-γ-lactone structures.
TY - JOUR
AU - Lorenc, Ljubinka B.
AU - Pavlović, Vladimir
AU - Juranić, Ivan
AU - Mihailović, Milhailo Lj.
AU - Bondarenko-Gheorghiu, Lidija G.
AU - Krstić, Natalija
AU - Dabović, Milan
PY - 1999
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4401
AB - The thermal and acid-catalyzed intramolecular rearrangement of the (Z)- and (E)-cyclodecene-1,4-dione compounds deriving from steroids, 2a,b and 3a,b, respectively, proceeds stereoselectively to give the corresponding configurationally different spiro-γ-lactone derivatives, the (5R,9R)-isomers 4a,b (from the (Z)-cyclodecenediones 2a,b) and the (5R,9S)-isomers 5a,b (from the (E)-cyclodecenediones 3a,b). The semiempirical MNDOAM1 and PM3 molecular orbital methods were applied to elucidate the possible mechanistic pathway of the observed intramolecular process leading to the spiro-γ-lactone structures.
PB - MDPI
T2 - Molecules
T1 - Stereoselective transformation of cyclodecene-1,4-dione systems, derived from steroids, to the corresponding spiro-g-lactones. A semiempirical MO Study
VL - 4
IS - 10
SP - 272
EP - 278
DO - 10.3390/41000272
ER -
@article{
author = "Lorenc, Ljubinka B. and Pavlović, Vladimir and Juranić, Ivan and Mihailović, Milhailo Lj. and Bondarenko-Gheorghiu, Lidija G. and Krstić, Natalija and Dabović, Milan",
year = "1999",
abstract = "The thermal and acid-catalyzed intramolecular rearrangement of the (Z)- and (E)-cyclodecene-1,4-dione compounds deriving from steroids, 2a,b and 3a,b, respectively, proceeds stereoselectively to give the corresponding configurationally different spiro-γ-lactone derivatives, the (5R,9R)-isomers 4a,b (from the (Z)-cyclodecenediones 2a,b) and the (5R,9S)-isomers 5a,b (from the (E)-cyclodecenediones 3a,b). The semiempirical MNDOAM1 and PM3 molecular orbital methods were applied to elucidate the possible mechanistic pathway of the observed intramolecular process leading to the spiro-γ-lactone structures.",
publisher = "MDPI",
journal = "Molecules",
title = "Stereoselective transformation of cyclodecene-1,4-dione systems, derived from steroids, to the corresponding spiro-g-lactones. A semiempirical MO Study",
volume = "4",
number = "10",
pages = "272-278",
doi = "10.3390/41000272"
}
Lorenc, L. B., Pavlović, V., Juranić, I., Mihailović, M. Lj., Bondarenko-Gheorghiu, L. G., Krstić, N.,& Dabović, M.. (1999). Stereoselective transformation of cyclodecene-1,4-dione systems, derived from steroids, to the corresponding spiro-g-lactones. A semiempirical MO Study. in Molecules
MDPI., 4(10), 272-278.
https://doi.org/10.3390/41000272
Lorenc LB, Pavlović V, Juranić I, Mihailović ML, Bondarenko-Gheorghiu LG, Krstić N, Dabović M. Stereoselective transformation of cyclodecene-1,4-dione systems, derived from steroids, to the corresponding spiro-g-lactones. A semiempirical MO Study. in Molecules. 1999;4(10):272-278.
doi:10.3390/41000272 .
Lorenc, Ljubinka B., Pavlović, Vladimir, Juranić, Ivan, Mihailović, Milhailo Lj., Bondarenko-Gheorghiu, Lidija G., Krstić, Natalija, Dabović, Milan, "Stereoselective transformation of cyclodecene-1,4-dione systems, derived from steroids, to the corresponding spiro-g-lactones. A semiempirical MO Study" in Molecules, 4, no. 10 (1999):272-278,
https://doi.org/10.3390/41000272 . .
