Synthesis and stereochemical investigations of novel nitrogen-containing 13alpha-estrone derivatives.
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.
Mernyák
Erzsébet
E
Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary.
Schneider
Gyula
G
Herbst-Irmer
Regine
R
Kubas
Melanie
M
Wölfling
János
J
D004970:Estrone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism
D004970:Estrone; D009584:Nitrogen