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Synthesis of bioactive natural compounds and their analogs.

Supervisor: prof. Ing. Ľubor Fišera, DrSc.


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Project description:The primary research objectives of this project are, firstly, to promote an innovative and interdisciplinary within the field of synthetic organic chemistry; secondly, to provide the practical ability to generate and utilize novel chemical synthetic methodologies and techniques to provide large quantities of natural products and structural analogs with biological activities of interest for the treatment of disease, the control of opportunistic pests and pathogens as well as other related health issues. In the key step, the chiral isoxazolidines prepared from sugar derived nitrones will be reduced to polyhydroxylated lactams (pyrrolidin-2-ones) that could be effective glycosidase inhibitors and also effective intermediates for the synthesis of pyrrolidine, pyrrolizidine and indolizidine alkaloids. The alternative synthesis of chiral polyhydroxylated pyrrolidin-2-ones from chiral gama-amino acids prepared by SmI2 induced diastereoselective reductive coupling of sugar derived nitrones with ethyl acrylate will be also used. The next goal is devoted the generation of anomerically pure nucleosides via the Vorbrüggen method as well to the study of the effect of Lewis acids on the regio- and diastereoselectivity of nitrone cycloadditions with alkynes. New synthetic strategies will be applied in the syntheses of biologically active natural compounds . The are two main objectives for the first period of the proposal: the first one being the cutting-edge research and development of new, reliable and powerful synthetic methodologies for construction of five and six membered oxa/aza heterocyclic skeletons with defined stereochemistry. The second one is study of diastereoselectivity of Pd(II)-catalyzed cyclizations of aminoalkenes and alkeneols. Following the recent results of our long term program, another aim of this project is focused on utilisation of intermediary formed sigma-palladium complexes in domino reactions with subsequent carbonylation and/or cross-coupling reaction.
Kind of project:VEGA ()
Department:Department of Organic Chemistry (IOCP FCFT)
Project identification:1/0236/09
Project status:Successfully completed
Project start date :01. 01. 2009
Project close date:31. 12. 2012
Number of workers in the project:2
Number of official workers in the project:0