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Syntheses of Zindoxifene and Analogues by Titanium‐Induced Oxo‐Amide Coupling
Author(s) -
fürstner Alois,
Jumbam Denis N.,
Seidel Günter
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19941270624
Subject(s) - chemistry , amide , indole test , titanium , stereochemistry , combinatorial chemistry , coupling (piping) , substitution (logic) , organic chemistry , mechanical engineering , computer science , engineering , programming language
Highly reactive titanium on graphite is used to reductively cyclize electron‐rich acylamino carbonyl compounds 7, 8, 12, 14 , and 16 to the corresponding indole derivatives 9, 10, 13, 15 , and 17 . Compound 9b is a known precursor of the mammary tumor‐inhibiting compound zindoxifene ( 2 ). The other products are new analogues of this anticancer drug, exhibiting the substitution pattern previously recognized to be essential for high pharmacological activity.