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Tomas Hudlicky: Research
Green Chemistry We have made environmentally benign reaction design one of our central themes in the Hudlicky group. The conversion of toxic aromatic waste into defined value-added products by chemoenzymatic means has been applied very successfully in our group and has yielded many total synthesis as well as commercial applications. We have also proposed a parameter (effective mass yield EMY) that allows the quantification of the degree of environmentally benignity of a synthetic sequence.
Amaryllidaceae Alkaloids Members of the amaryllidaceae alkaloids (e.g. Pancratistatin) are known to possess high anti-tumor activities, which makes them very interesting targets for the synthetic organic chemist. In the last several years, we have completed a total synthesis of (-)-pancratistatin and (-)-narciclasine, both by chemoenzymatic means. We are currently working on a total synthesis of 7-deoxypancratistatin as well as an optimization of previous approaches, with the overall goal of preparing these alkaloids in less than ten steps.
A long term goal in
the Hudlicky group has been a enantioselective total synthesis of
morphine and the morphinan skeleton. Inositols Our group has successfully prepared several of the nine Inositols as well as di-and oligomeric analogues. We have proven that these oligomers possess very interesting properties like their helical tertiary structure.We are currently working on the preparation of amino Inositol derivatives which are expected to exhibit similar structural features as well as enzyme inhibition properties.
Electrochemistry As a part of environmentally benign
reaction design the Hudlicky group has exploited the possibility of
substituting steps which include toxic reagents by electrochemical
means. We have successfully shown that transformations like mCPBA
epoxidation and tetrabutyltinhydride reductions can also be achieved
by electrochemical methods.
Microbial Dihydroxylation Chiral
synthons obtained by microbial dihydroxylation of halogenated
aromatic compounds have been applied as starting materials for a
variety of syntheses in our group. Other Research Interests Besides the topics mentioned above, our group is active in a variety of fields. This includes radical cyclizations, Diels Alder chemistry, approaches towards other natural products (e.g. TaxolTM) and many more.
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