Mernyák Erzsébet, Schneider Gyula, Herbst-Irmer Regine, Kubas Melanie, Wölfling János
Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary.
Steroids. 2006 Jul;71(7):558-64. doi: 10.1016/j.steroids.2006.01.013. Epub 2006 Apr 18.
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.
从裂环醛8和单取代或双取代苯胺9出发，高效合成了新型13α-雌酮系列的四氢喹啉11和N-芳基d-高同系物衍生物12。环化反应的化学选择性取决于苯胺中取代基的性质。所有转化均以高度立体选择性的方式进行，仅产生一种非对映异构体。稠合的11和d-高同系物衍生物12在固态时均具有常见的C环椅式构象。
