Factors Governing the Relative Stabilities of the C/D Cis and Trans Ring Junctures in Δ8-11-keto Steroids

Donald G. Patterson, Carl Djerassi, Young Yuh, Norman L. Allinger

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

Pure 14α and 14β epimers of Δ8-11-keto steroids with different 17β-alkyl groups were prepared and the position of their base-catalyzed equilibrium established by gas-liquid phase chromatography. In contrast to 15-keto steroids, where the nature of the 17β substituents crucially affects the cis/trans hydrindanone equilibrium, the 14β (C/D cis) isomer is greatly favored in the present series irrespective of the nature of the C-17 substituent. Using a previously described force-field method, the energies and conformations of the cis and trans isomers of the Δ8-11-keto steroids were calculated and found to be in reasonable agreement with the experimentally established values.

Original languageEnglish (US)
Pages (from-to)2365-2370
Number of pages6
JournalJournal of Organic Chemistry
Volume42
Issue number14
DOIs
StatePublished - Jul 1 1977

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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