1. The use of symmetry in enantioselective synthesis: four pairs of chrysene enantiomers prepared from 19-nortestosterone.
- Author
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Stastna E, Rath NP, and Covey DF
- Subjects
- Androgens chemistry, Chromatography, Thin Layer, Chrysenes analysis, GABA Agonists analysis, GABA Antagonists analysis, Humans, Magnetic Resonance Spectroscopy, Neurotransmitter Agents analysis, Pregnanes chemistry, Receptors, GABA metabolism, Stereoisomerism, Chemistry, Pharmaceutical methods, Chrysenes chemical synthesis, GABA Agonists chemical synthesis, GABA Antagonists chemical synthesis, Nandrolone chemistry, Neurotransmitter Agents chemical synthesis
- Abstract
Expansion of the D-ring of 19-norsteroids with incorporation of the steroid C-18 methyl group into a newly formed six-membered ring provides easy access to the chrysene ring system. By taking advantage of the symmetry of the chrysene ring system and avoiding meso chrysene intermediates, four optically pure 2,8-difunctionalized (C-2 hydroxyl group and C-8 oxo group) hexadecahydrochrysene diastereomers, and their corresponding optically pure enantiomers were prepared from 19-nortestosterone. The eight chrysene stereoisomers are of interest as starting materials for preparing chrysene analogues of physiologically important neurosteroids.
- Published
- 2011
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