Synthesis of novel steroid-tetrahydroquinoline hybrid molecules and d-homosteroids by intramolecular cyclization reactions

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Synthesis of novel steroid-tetrahydroquinoline hybrid molecules and d-homosteroids by intramolecular cyclization reactions

Magyar, Angéla; Wölfling, János; Kubas, Melanie; Cuesta Seijo, Jose Antonio; Sevvana, Madhumati; Herbst-Irmer, Regine; Forgó, Péter; Schneider, Gyula

Steroids, 05/2004, Volume: 69, Issue: 5

Journal Article

Steroidal aryliminium salts were prepared from d- seco-pregnene aldehyde 2b, and their BF 3·OEt 2-catalyzed reactions were studied. The nature of the substituent R 1 in the anilines 3– 6 essentially influenced the chemoselectivity. Using unsubstituted 3, 4-methoxy- ( 4) or 4-bromoaniline ( 5), different tetrahydroquinoline derivatives 7a– 13a via intramolecular hetero Diels-Alder reaction were formed. In the case of 4-nitroaniline ( 6) the N-arylamino- d-homopregnane ( 14a) were also obtained. We assume, that an intramolecular Prins reaction led to this type of fluoro- d-homosteroid. The main products represent a new class of tetrahydroquinolino-androstenes.

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