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USE OF COUPLING REACTIONS IN THE SYNTHESIS OF POTENTIALLY BIOLOGICALLY ACTIVE COMPOUNDS
Hessler, Filip ; Kotora, Martin (advisor) ; Pour, Milan (referee)
This work consists of three parts, each dealing with the synthesis of different biologically active compound, using reactions mediated by transition metals. 1. Ferrocene conjugates with various types of natural or biologically active compounds have been studied intensively for their new interesting properties compared to the model compounds. It was decided to synthesize a new steroid containing ferrocene - ferrocenestrone, planned with regard to its possible activity against breast cancer cells. Although several conjugates of steroids with ferrocene have been prepared, the cyclopentadienyl ring has not been the integral part of the steroid skeleton in any of them. Ferrocenestrone, an analog of estrone, however contains ferrocene in place of the aromatic A-ring. The approach to the ferrocene-steroid framework construction was based on transition metal mediated reactions starting from a suitably substituted chiral ferrocene. The methods used were: zirconocene-mediated oxidative additions with successive alkylation sequences, palladium- catalyzed cross-coupling reactions, ruthenium-catalyzed skeletal rearrangements (enyne metathesis), palladium and iridium catalyzed hydrogenations etc. Also selective oxidation and subsequent borane reduction was used for the final change of skeletal configuration....
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