{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Stastna E"],"funding":["NIGMS NIH HHS"],"pagination":["4685-94"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC3154374"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["9(12)"],"pubmed_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."],"journal":["Organic & biomolecular chemistry"],"pubmed_title":["The use of symmetry in enantioselective synthesis: four pairs of chrysene enantiomers prepared from 19-nortestosterone."],"pmcid":["PMC3154374"],"funding_grant_id":["P01 GM047969-19","GM47969","P01 GM047969"],"pubmed_authors":["Stastna E","Covey DF","Rath NP"],"additional_accession":[]},"is_claimable":false,"name":"The use of symmetry in enantioselective synthesis: four pairs of chrysene enantiomers prepared from 19-nortestosterone.","description":"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.","dates":{"release":"2011-01-01T00:00:00Z","publication":"2011 Jun","modification":"2024-11-09T04:07:11.042Z","creation":"2019-03-27T03:07:54Z"},"accession":"S-EPMC3154374","cross_references":{"pubmed":["21541379"],"doi":["10.1039/c1ob05385j"]}}