Palladium-catalyzed diaminocarbonylation: synthesis of androstene dimers containing 3,3’ - or 17,17’-dicarboxamide spacers

Kiss, Mercédesz and Mahó, Sándor and Böddi, Katalin and Boros, Borbála and Kollár, László (2015) Palladium-catalyzed diaminocarbonylation: synthesis of androstene dimers containing 3,3’ - or 17,17’-dicarboxamide spacers. MONATSHEFTE FÜR CHEMIE, 146. pp. 357-364. ISSN 0026-9247

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Abstract

Novel androstene-based dimers linked through A- and D-ring with 3,3′- and 17,17′-dicarboxamide spacers, were synthesized via palladium-catalyzed aminocarbonylation. Androstane derivatives possessing either 3-iodo-3,5-diene or 17-iodo-16-ene functionality were used as substrates in the presence of palladium-phosphine in situ catalysts and aliphatic and aromatic diamines as N-nucleophiles. Since androst-4-ene-3,17-dione was used as starting material, a multistep synthesis including protection/deprotection of one of the keto functionalities (3-one or 17-one) as ethylene ketals, transformation of the other keto group to iodoalkene functionality via its hydrazone, and palladium-catalyzed aminocarbonylation of the iodoalkene functionality was used. In this way, new dimeric compounds possessing a keto functionality were obtained in moderate-to-good isolated yields, via highly chemoselective reactions, under relatively mild conditions.

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