Stereoselective transformation of cyclodecene-1,4-dione systems, derived from steroids, to the corresponding spiro-g-lactones. A semiempirical MO Study
Authors
Lorenc, Ljubinka B.Pavlović, Vladimir
Juranić, Ivan
Mihailović, Milhailo Lj.
Bondarenko-Gheorghiu, Lidija G.
Krstić, Natalija
Dabović, Milan
Article (Published version)
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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.
Keywords:
Acid catalysis / AM1 / Molecular rearrangement / PM3 / seco-SteroidsSource:
Molecules, 1999, 4, 10, 272-278Publisher:
- MDPI
DOI: 10.3390/41000272
ISSN: 1420-3049
WoS: 000083092100002
Scopus: 2-s2.0-4344676754
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IHTMTY - 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 . .