Department of Chemistry
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C. Skorski,
Admininstrative Assistant
Dept. of Chemistry
Brock University
500 Glenridge Ave.
St. Catharines, ON
Canada, L2S 3A1
Tel: (905) 688-5550 x3406
Fax: (905) 682-9020
E-mail: cskorski@brocku.ca


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.

 


Morphine

A long term goal in the Hudlicky group has been a enantioselective total synthesis of morphine and the morphinan skeleton. 
It is envisioned that short synthetic route to the title alkaloid will open doors for the preparation of a variety of analogs which are not easily accessible by functional group transformation starting from the parent alkaloid itself.

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.
We are also working on the selective removal of protecting groups by electrochemistry as well as electrochemical cyclizations.

 

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.
We are currently also studying the substrate specificity of the enzymes responsible for this transformation as well as the influence of remote chiral centers on the outcome of the hydroxylation reaction.

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.