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Cross-coupling Reactions for Steroid Modification: from Arylation to Macrocycle Syntheses

Lukashev N., Averin A., Latyshev G., Donez P., Ranyuk E., Beletskaya I.

Polish Journal of Chemistry

2006

Vol. 80, nr 4

559-572

The Suzuki-Miyaura coupling of 4- and 6-halosteroids affords good to excellent yields of potential aromatase inhibitors.While the reaction with 4- and 6-bromo derivatives is catalyzed by Pd(PPh3)2Cl2, the coupling with 6-chloro steroid (chlormadinone acetate) requires the use of Pd(dppb)Cl2 or Pd(dppf)Cl2. The palladium-catalyzed amination of bis(3-bromophenyl) ether of (5_)-cholane-3,24-diol with different polyamines leads to new macrocycles comprising one steroid and one polyamine fragments. Possibility of synthesis of macrocyclodimers containing two steroid and two polyamine fragments have been investigated.