Stereoselective Transformation of Cyclodecene-1,4-dione Systems, Derived from Steroids, to the Corresponding spiro-γ-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...

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Veröffentlicht in:	Molecules (Basel, Switzerland) Switzerland), 1999-10, Vol.4 (10), p.272-278
Hauptverfasser:	Lorenc, Ljubinka, Pavlovich, Vladimir, Juranich, Ivan, Mihailovich, Mihailo Lj, Bondarenko- Gheorghiu, Lidija, Krstich, Natalija, Dabovich, Milan
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container_title	Molecules (Basel, Switzerland)
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creator	Lorenc, Ljubinka Pavlovich, Vladimir Juranich, Ivan Mihailovich, Mihailo Lj Bondarenko- Gheorghiu, Lidija Krstich, Natalija Dabovich, Milan
description	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.
doi_str_mv	10.3390/41000272
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title	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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