Synthesis and stereochemical investigations of novel nitrogen-containing 13α-estrone derivatives

E. Mernyák, G. Schneider, Regine Herbst-Irmer, Melanie Kubas, J. Wölfling

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Novel tetrahydroquinoline 11 and N-aryl d-homo derivatives 12 in the 13α-estrone series were synthesized effectively, starting from the secoaldehyde 8 and mono- or disubstituted anilines 9. The chemoselectivity of the cyclization reactions depended upon the nature of the substituents in the anilines. All transformations proceeded in a highly stereoselective manner, yielding only one diastereomer. Condensed 11 and d-homo derivatives 12 both have the usual ring C chair conformation in the solid state.

Original languageEnglish
Pages (from-to)558-564
Number of pages7
JournalSteroids
Volume71
Issue number7
DOIs
Publication statusPublished - Jul 2006

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Aniline Compounds
Estrone
Nitrogen
Derivatives
Cyclization
Conformations

Keywords

  • 13α-Estrone
  • Chemo- and stereoselective synthesis
  • d-Secosteroid
  • Hetero Diels-Alder reaction
  • Heterocyclic steroids

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology
  • Molecular Biology

Cite this

Synthesis and stereochemical investigations of novel nitrogen-containing 13α-estrone derivatives. / Mernyák, E.; Schneider, G.; Herbst-Irmer, Regine; Kubas, Melanie; Wölfling, J.

In: Steroids, Vol. 71, No. 7, 07.2006, p. 558-564.

Research output: Contribution to journalArticle

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