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.
Original language | English |
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Pages (from-to) | 4685-4694 |
Number of pages | 10 |
Journal | Organic and Biomolecular Chemistry |
Volume | 9 |
Issue number | 12 |
DOIs | |
State | Published - Jun 21 2011 |