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Molecules 1999, 4(10), 272-278; doi:10.3390/41000272
Article

Stereoselective Transformation of Cyclodecene-1,4-dione Systems, Derived from Steroids, to the Corresponding spiro-γ-lactones. A Semiempirical MO Study

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Received: 21 June 1999; Accepted: 20 July 1999 / Published: 12 September 1999
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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.
Keywords: seco-Steroids; Molecular rearrangement; Acid catalysis; AM1; PM3 seco-Steroids; Molecular rearrangement; Acid catalysis; AM1; PM3
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Lorenc, L.; Pavlovich, V.; Juranich, I.; Mihailovich, M.L.; Bondarenko- Gheorghiu, L.; Krstich, N.; Dabovich, M. Stereoselective Transformation of Cyclodecene-1,4-dione Systems, Derived from Steroids, to the Corresponding spiro-γ-lactones. A Semiempirical MO Study. Molecules 1999, 4, 272-278.

AMA Style

Lorenc L, Pavlovich V, Juranich I, Mihailovich ML, Bondarenko- Gheorghiu L, Krstich N, Dabovich M. Stereoselective Transformation of Cyclodecene-1,4-dione Systems, Derived from Steroids, to the Corresponding spiro-γ-lactones. A Semiempirical MO Study. Molecules. 1999; 4(10):272-278.

Chicago/Turabian Style

Lorenc, Ljubinka; Pavlovich, Vladimir; Juranich, Ivan; Mihailovich, Mihailo L.; Bondarenko- Gheorghiu, Lidija; Krstich, Natalija; Dabovich, Milan. 1999. "Stereoselective Transformation of Cyclodecene-1,4-dione Systems, Derived from Steroids, to the Corresponding spiro-γ-lactones. A Semiempirical MO Study." Molecules 4, no. 10: 272-278.


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