Diels Alder reaction between two relevant green chiral precursors. Approach to natural product like-compounds.

CARRAU, G.; VEIGA, N. ; SUESCUN, L.; GIRI, G. F.; SUÁREZ, A. G.; SPANEVELLO, R. A.; GONZÁLEZ, D.

Buzios

Encuentro; 16th Brazilian Meeting on Organic Synthesis; 2015

SociedadE BrasileIra de Química

The quest for strategies to rapidly build structural diversity, often targeting complex chiral molecules that resemble natural products has emerged as route for the discovery of new bioactive molecules.These structures are often called natural product like-compounds (NPLC) and typically comprise molecules with several rings, stereochemically defined chiral centers and double bonds.1-2 The interest in NPLC becomes relevant when they are constructed by short synthetic sequences that also allow for stereodivergence and for ease modification of substituents. NPLC incorporate the advantages of natural products such as structural complexity and diversity along with the benefits of typical synthetic pharmaceutical molecules: ease of preparation and structural modification. Our groups in Argentina and Uruguay have tradition on working in green chemistry and biocatalysis. The group in Argentina has made several contributions to synthetic methodologies working in the preparation and modification of optically pure levoglucosenone from the pyrolysis of cellulose. The Uruguayan group has a tradition inbiocatalysis and exploitation in synthesis of homochiral cyclohexadiene diols such as compound 1 obtained by microbial oxidation of aromatics.