Syntheses of Zindoxifene and Analogues by Titanium-Induced Oxo-Amide Coupling

Fürstner, Alois; Jumbam, Denis N.; Seidel, Günter

doi:10.1002/cber.19941270624

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Syntheses of Zindoxifene and Analogues by Titanium-Induced Oxo-Amide Coupling

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Fürstner, Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Jumbam, Denis N.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Seidel, Günter
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fürstner, A., Jumbam, D. N., & Seidel, G. (1994). Syntheses of Zindoxifene and Analogues by Titanium-Induced Oxo-Amide Coupling. Chemische Berichte, 127(6), 1125-1130. doi:10.1002/cber.19941270624.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-A4A2-A

Abstract

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.