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.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Androgens / chemistry
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Chemistry, Pharmaceutical / methods*
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Chromatography, Thin Layer
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Chrysenes / analysis
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Chrysenes / chemical synthesis*
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GABA Agonists / analysis
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GABA Agonists / chemical synthesis*
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GABA Antagonists / analysis
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GABA Antagonists / chemical synthesis*
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Humans
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Magnetic Resonance Spectroscopy
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Nandrolone / chemistry*
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Neurotransmitter Agents / analysis
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Neurotransmitter Agents / chemical synthesis*
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Pregnanes / chemistry
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Receptors, GABA / metabolism
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Stereoisomerism
Substances
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Androgens
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Chrysenes
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GABA Agonists
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GABA Antagonists
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Neurotransmitter Agents
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Pregnanes
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Receptors, GABA
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Nandrolone