title: The use of symmetry in enantioselective synthesis: four pairs of chrysene enantiomers prepared from 19-nortestosterone.
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.
authors.affiliation: Department of Developmental Biology, Campus Box 8103, Washington University in St. Louis, School of Medicine, 660 S. Euclid Ave., St. Louis, MO 63110, USA.
authors.forename: Eva
authors.initials: E
authors.lastname: Stastna
authors.forename: Nigam P
authors.initials: NP
authors.lastname: Rath
authors.forename: Douglas F
authors.initials: DF
authors.lastname: Covey
mesh_terms: D000728:Androgens / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D002855:Chromatography, Thin Layer; D002911:Chrysenes / Q000032:analysis / Q000138:chemical synthesis*; D018755:GABA Agonists / Q000032:analysis / Q000138:chemical synthesis*; D018756:GABA Antagonists / Q000032:analysis / Q000138:chemical synthesis*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D009277:Nandrolone / Q000737:chemistry*; D018377:Neurotransmitter Agents / Q000032:analysis / Q000138:chemical synthesis*; D011278:Pregnanes / Q000737:chemistry; D018079:Receptors, GABA / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D000728:Androgens; D002911:Chrysenes; D018755:GABA Agonists; D018756:GABA Antagonists; D018377:Neurotransmitter Agents; D011278:Pregnanes; D018079:Receptors, GABA; D009277:Nandrolone