Faculty of Chemical and Food Technology
Department/Institute: Department of Organic Chemistry
Contact person: prof. Ing. Tibor Gracza, DrSc.
Contact: +421 2 5249 5410
web page: http://www.chtf.stuba.sk/koch/gracza.php
The Laboratory of natural products chemistry deals with the synthesis of selected natural products of biomedical significance and the development of synthetic methodology for the construction of complex, biologically intriguing molecules. Total synthesis technology platforms, deploying new methodology in the area of palladium(II)-catalysed cyclisations of unsaturated polyols and aminoalcohols in particular.
Design, synthesis and antiproliferative activity of tetrahydrofurans related to (+)-varitriol
Design, synthesis and antiproliferative activity of tetrahydrofurans related to natural (+)-varitriol. Notably cytotoxic varitriol towards selected human cell lines serves as lead structure for synthesis and rational design of new substances with high activity and selectivity toward cancer cells. Development of new synthetic methodology for synthesis of tetrahydrofuran compounds with defined configuration at all stereogenic centres and its application in the syntheses of analogues, hmologues and vinylogues of varitriol. Study of structure-activity relationship (SAR, QSAR). Investigation of molecular targets and mechanism of action for molecular design.
Vega 1/0115/10, 2009-2011
Stereoselective palladium catalysed cyclisations and cross-coupling reactions in natural product synthesis
Development of new synthetic methodology for synthesis of oxa- and azaheterocyclic compounds with defined configuration at all stereogenic centers. The application of the methodologies in the syntheses of natural products and biologically interesting compounds.
Study of chemo-, diastereo- and substrate selectivity of palladium(II)-catalysed cyclisation of unsaturated polyols. Exploration of the reaction by trapping of intermediary sigma-alkyl Pd(II)-complex in the domino reaction with subsequent C-C, C-O, C-N cross-coupling reactions. The application of the domino reactions for construction of dioxa[2.2.1]bicyclic skeletons, polyhydroxylated tetrahydrofurans, tetrahydropyrans, pyrrolidines and piperidines with defined stereochemistry. Synthetic strategies will be applied in the total syntheses of natural C-15 acetogenins, goniothalesdiols, varitriol and deoxyanhydroaminoalditols. Synthesis of modified isoxazolidinyl nucleosides using Pd-catalysed cross-coupling reactions.
Stereoselective Pd(II)-catalysed bicyclisation in the natural product synthesis
Development of new synthetic methodology for construction of the dioxa[2.2.1]bicyclic skeleton, polyhydroxyl substituted tetrahydrofuran derivatives with 2,3-trans arrangement of substituents. Their application in the syntheses of natural products and biologically interesting compounds.
Optimisation of the total synthesis of (+)-varitriol, natural tetrahydrofuran possesing high cytotoxic aktivity toward selected human tumor cell lines. The synthesis of the l-xylo-4-O-benzylhex-5-en-2,3,4-triol using chiral pool approach from d-glucose and dimethyl l-tartrate. Study of chemo-, diastereo- and substrate selectivity of palladium(II)-catalysed bicyclisation of unsaturated diols. Pd(II)-catalysed bicyclisation of diols with E- and Z-symetrically disubstituted C=C double bond. The application of the stereocontrolled Pd-catalysed bicyclisations in the syntheses of compounds isolated from marine organisms. Synthetic study towards natural C-15 acetogenins.
Domino reactions in the ionic liquids and their application in the natural product synthesis
Development of new strategies for stereoselective funcionalization of C=C double bond of alkenes with introduction of O- and/or N-functions. Study of new Pd(II)-catalyzed oxy-/aminocarbonylations and cross-coupling domino reactions in enviroment frendly ionic liquids. Application of Pd-domino reactions in the total syntheses of natural compounds and biologically interesting compounds.
Analytical laboratory, LC-MS chromatograf
Synthetical laboratory, preparatory MPLC chromatograf
Synthetic laboratórium, polarimeter
Automatic destilation equipment