Kirill Tchabanenko

Dr

  • Room 01.420 - David Keir Building

    United Kingdom

20042019

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Research Statement

•1. Research progress.

Since my appointment for the lectureship position in August 2008 I initiated research in a new original area of organic chemistry centred around new applications of the 1,3-dipolar cycloaddition of pyrilium ykides in synthesis. Progress was made in the following:

•- Synthesis of tropolone based natural products via the 1,3-dipolar cycloaddition reaction. A concise approach to a family of complex natural products was developed and a short synthesis of a simplified structure vas published in Tetrahedron Letters, 2010, 51, 86-88.

•- Development of the stereoselective cycloaddition of pyrylium ylides with chiral enamides. Positive results are currently being written-up as a manuscript due for submission in early July 2011.

•- Development of organocatalytic 1,3-dipolar cycloaddition reactions of pyrylium ylides. Screening of over 20 different organocatalysts, most of which were prepared in our lab, has identified primary amine-thiourea organocatalysts as the best candidates for the asymmetric organocatalytic cycloaddition reactions. Catalyst optimisation is currently under way.

•- Synthesis of Englerin A inspired scaffolds. New methodology was developed for synthesis of new medicinal targets inspired by a complex biologically active natural product. A small library of compounds is currently being prepared. We hope to have this ready for biological testing before the end of 2011.

The results were presented on two symposiums in QUB (July 2009 dedicated to the Honorary Degree Nomination of professor Amos B. Smith and in June 2010 Medicinal Chemistry Symposium jointly with the University of Malaya). Presentation was also made on the Gregynog Organic Chemistry Conference in September 2009. A poster presentation will be made on the RSC Synthetic Organic Chemistry meeting in Cambridge, July 2011.

•2. Research plans.

Short term. New stereoselective cycloaddition reactions of pyrylium ylides with chiral vinyl sulfoxides will be investigated within the next academic year. Further development of novel organocatalysts and synthesis of Englerin A analogues will be undertaken.

Long term. New organocatalysts will be applied in novel organocatalytic pericyclic reactions, such as:

•- Diels-Alder type cycloadditions;

•- Nazarov-type cyclisations;

•- Electrocyclisations;

•- Cycloadditions of oxy-allyl cations.

Development of new organocatalysts and new organocatalytic reactions is at the forefront of the research in the SynBioc Cluster in QUB. Commonly seen as 'green' these methods will make a strong contribution to the Queen's investment in development of environmentally friendly technologies. Also, being at the forefront of the current organic chemistry research, this research is guaranteed to generate high impact publications in top scientific journals.

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