Synthesis of Complex Molecules from Simple Aromatic Precursors

在这个由化学部化学合成计划资助的项目中，加州大学欧文分校化学系的Vanderwal教授将继续开发Zincke醛-吡啶盐开环氨解的产物-作为复杂分子合成的有用试剂。例如，Zincke醛将被用作吡啶的易官能化替代品，从而实现多取代吡啶的受控制备。以前开发的从Zincke醛的级联周环反应中获得复杂多环胺的方法将被应用于生物碱钩吻碱、苦杏仁碱A和B的合成。最后，在一项新的冒险中，将利用Himbert芳烃/烯丙烯环加成反应来生成复杂的结构。这项工作通常旨在提高从现成的起始材料组装复杂的、有附加值的化合物的效率。这些研究的结果将对任何受益于化学合成的应用科学领域产生积极影响，包括药物开发、材料科学等。该项目将为本科生和研究生提供科研实训基地。为该项目提供的资助也将支持UCI-LEAPS(实验室实验和物理科学活动)计划，该计划吸引当地中学生在大学化学和物理实验室进行为期一天的体验。

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.