Synthesis and stereochemical investigations of novel nitrogen-containing 13alpha-estrone derivatives
Erzsébet Mernyák1, Gyula Schneider, Regine Herbst-Irmer
1Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary.
Abstract:
Novel tetrahydroquinoline 11 and N-aryl d-homo derivatives 12 in the 13alpha-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.
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