In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Vanderwal of the Department of Chemistry at UC Irvine will continue to develop Zincke aldehydes - the products of the ring-opening aminolysis of pyridinium salts - as useful reagents for complex molecule synthesis. For example, Zincke aldehydes will be used as readily functionalizable surrogates to pyridines, enabling the controlled preparation of polysubstituted pyridines. Previously developed methods to access complex polycyclic amines from cascade pericyclic reactions of Zincke aldehydes will be applied to the synthesis of the alkaloids gelsemine and alsmaphorazines A and B. Finally, in a new venture, the Himbert arene/allene cycloaddition reaction will be exploited for the generation of complex architectures.
This work generally aims to improve the efficiency of assembly of complex, value-added compounds from readily available starting materials. The results of these studies will positively impact any area of applied science that benefits from chemical synthesis, including pharmaceutical development, materials science, and more. This project will provide a research training ground for undergraduate and graduate students. The grant provided in support of this project will also support the UCI-LEAPS (Laboratory Experiments & Activities in the Physical Sciences) program that brings in local middle school students for day-long experiences in university chemistry and physics laboratories.
