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Synthesis of Unusual Bridged Steroid Alkaloids by an Iminium Ion Induced 1,5‐Shift of a Benzylic Hydride
Author(s) -
Wölfling János,
Frank Éva,
Schneider Gyula,
Tietze Lutz F.
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990115)38:1/2<200::aid-anie200>3.0.co;2-l
Subject(s) - iminium , hydride , chemistry , amine gas treating , steroid , derivative (finance) , ion , medicinal chemistry , combinatorial chemistry , organic chemistry , metal , biochemistry , hormone , financial economics , economics
Unusual steroid alkaloids form unexpectedly in a domino process (see scheme) by reaction of an aldehydic derivative readily available from estrone with anilines. The key step of this reaction is presumably an unusual 1,5‐hydride shift from a benzylic CH group to an iminium ion under formation of a carbocationic center and a secondary amine that subsequently react together.