IQUIR   05412
INSTITUTO DE QUIMICA ROSARIO
Unidad Ejecutora - UE
congresos y reuniones científicas
Título:
Sailing to Ithaca in a Sugar Boat
Autor/es:
ROLANDO A. SPANEVELLO
Lugar:
Sao Pedro, Brasil
Reunión:
Congreso; 13th Brazilian Meeting on Organic Síntesis; 2009
Institución organizadora:
Sociedade Brasileira de Química
Resumen:
A wide variety of biological functions emerge through molecular recognition which requires strict matching of chirality. Therefore, the synthesis of enantiomerically pure products plays an important role in the development of new drugs, agrochemicals, polymers, etc. Synthetic chemists have devised different methods to synthesize this type of substances. One of the most widely use strategies to obtain optically pure organic compounds is to take advantage of the chiral pool. Among the plethora of natural molecules, carbohydrates are the most prominent members of the chiral pool since they are major constituents of all foremost structural molecules in living systems. They are obtained from renewable resources in high enantiomeric purity and their molecular framework can exert an efficient regio and stereocontrol on different chemical processes. Monosaccharide derivatives, bearing an electron withdrawing group in a cyclic alpha, beta  unsaturated system, are unquestionable useful building blocks. We will describe our progress in the synthesis of pentalenolactone, a selective glyceraldehyde-3-phosphate dehydrogenase inhibitor in trypanosome and how the dead ends and detours that we encountered in our way led us to explore a nonsymmetrical ozonolysis reaction.But this was not the last stop in the journey to our Ithaca, because we also learnt that to meet the demand of a growing world population there is a need for the sciences constantly to reassess and promote less intensive trends in resource utilization. The role of chemistry is essential in ensuring that our next generations of chemicals, materials, and energy are more sustainable than the current generation. Worldwide demand for environmentally friendly chemical processes and products requires the development of novel and cost-effective approaches to pollution prevention and the use of renewable carbon to supply the world’s chemical needs. One of the most attractive concepts in chemistry for sustainability is Green Chemistry. Taking this concept as our compass to guide our future steps we devised a synthetic strategy to transform a small sugar derived building block, obtained from the pyrolysis of cellulose-containing materials such as waste paper, into a novel class of chiral auxiliaries and proved their effectiveness in asymmetric induction.