The use of symmetry in enantioselective synthesis: Four pairs of chrysene enantiomers prepared from 19-nortestosterone

Eva Stastna, Nigam P. Rath, Douglas F. Covey

Research output: Contribution to journalArticle

7 Scopus citations

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 languageEnglish
Pages (from-to)4685-4694
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number12
DOIs
StatePublished - Jun 21 2011

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