SUMMARY OF THE RESEARCH LINES

 

Enantioselective synthesis of  natural products and polymers.

 

Asymmetric molecules are synthesized employing readily available natural products (mainly sugars) as chiral templates. This strategy, known as enantioselective synthesis is involved in the two following lines of research:

I)      The preparation of reactive intermediates as precursors of thiosugars, carbocycles and heterocycles, and

II)   The synthesis of bifunctional, chiral monomers and their stereocontrolled polymerization to obtain stereoregular polymers.

Regarding the line I, we are studying the enantispecific synthesis of sugar derived enones (dihydropyranones), and their use as Michael acceptors of thiols and carbanions. These reactions lead to thodisaccarides (enzyme inhibitors) and branched chain sugars. The dihydropyranones are also employed in Diels-Alder cycloadditions and heterocycloadditions, to obtain carbocycles and heterocycles, precursors of natural products and molecules that are expected to display varied biological activities.

The use of carbohydrates and amino acids as a renewable source of biodegradable polymers is important from the point of view of the environmental safety. For this reason we are working on the synthesis of stereoregular polyamides and polyesters as potentially biodegradable materials. In addition, the stereocontrolled polymerizations should lead to optically active, stereoregular polymers having convenient physic and mechanical properties. Thus, polyamides of AB- and AABB-types with regio and stereoregular chains are synthesized. Also, the stereocontrolled homo- and co-polymerization of 1,6-aldonolactones are conducted to produce stereoregular, chiral polyesters, analogous of versatile materials of biomedical applications.

 

Keywords

Enantioselective synthesis, carbohydrates, stereoregular polyamides, stereoregular polyesters, thiosugars, chiral carbocycles and heterocycles.