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Palladium catalyzed synthesis of benzannulated steroid spiroketals

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Abstract

Nine cytotoxic [5/7] and [6/6] benzannulated steroid spiroketals were synthesized by palladium catalyzed spiroketalization of 5α and 5β-alkynediols derived from testosterone, diosgenin and cholesterol. The regioselectivity of the spiroketalization reaction is decisively influenced by the α or β-orientation of the hydroxyl group at C-5. NMR and single crystal X-ray diffraction corroborated the structure of the obtained compounds. Compounds bearing a cholestane skeleton exhibited higher cytotoxicity against U251 and T47D cells, and the BrdU incorporation assay suggests that the synthesized spiroketals inhibit cell proliferation.

Graphical abstract: Palladium catalyzed synthesis of benzannulated steroid spiroketals

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Article information


Submitted
17 Oct 2019
Accepted
19 Dec 2019
First published
19 Dec 2019

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Palladium catalyzed synthesis of benzannulated steroid spiroketals

M. C. Mayorquín-Torres, J. C. González-Orozco, M. Flores-Álamo, I. Camacho-Arroyo and M. A. Iglesias-Arteaga, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02255D

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