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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....
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...
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