Seminar (organic): Patrick J. Guiry, University College Dublin

Patrick J. Guiry
Centre for Synthesis and Chemical Biology
School of Chemistry and Chemical Biology
University College Dublin

Recent Results in Total Synthesis and Asymmetric Catalysis From Dublin

Asymmetric catalysis, one approach for the preparation of enantiomerically pure compounds and the focus of research in both academic and industrial laboratories, is an attractive technology as a small amount of enantiomerically pure material can produce large quantities of enantiomerically enriched or enantiopure material. Research in asymmetric catalysis todate highlights the difficulty in finding a 'universal' ligand suitable for a wide spectrum of reactions and substrates. For this reason the preparation and testing of new ligands for asymmetric catalysis is an active research field.

This presentation will describe the synthesis of C2- and non-C2-symmetric analogues of our bis-oxazoline ligands 1 and their application in the Nozaki-Hiyama-Kishi allylation, crotylation, methallylation and homoallenylation of aldehydes. In addition, the products of homoallenylation (β-allenols) will be tested as substrates for a series of reactions in order to study their usefulness in synthetic chemistry.

The synthesis and biological evaluation of Lipoxin A4 analogue 2, and the subsequent development of synthetic methodology applied to the asymmetric synthesis of natural products, e.g. pheromone 3 and (-)-frontalin 4, will also be discussed.