[Synthesis of estrone derivatives containing different halogens and/or heterocyclic moieties].
New compounds derived from the 3-methyl and 3-benzyl ethers of a D-secoestrone aldehyde were synthesized. In the presence of different Lewis acids D-homosteroids could form. These reactions which can be explained by an intramolecular Prinstype mechanism follow high stereoselectivity and reactivity and lead to compounds containing 16 beta-oriented halogens in the sterane skeleton. The formation and reaction of the imines derived from the aldehyde and aniline as well as substituted anilines provide a highly efficient access to steroid derivatives. The steroid alkaloids are of pharmacological interest.
Frank
E
E
Szegedi Tudományegyetem, Szerves Kémiai Tanszék, Szeged, Dóm tér 8.-6720.
Wölfling
J
J
Schneider
G
G
D004970:Estrone / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D006219:Halogens; D006571:Heterocyclic Compounds; D015394:Molecular Structure
D006219:Halogens; D006571:Heterocyclic Compounds; D004970:Estrone