CAREER: Efficient Synthesis of Biologically Relevant Cyclic and Polycyclic Terpenoid Compounds Using Alkyne Cyclizations

有了这个职业奖，合成计划支持内华达大学里诺分校的韦斯利A.查利福教授的研究。Chalifoux教授开发了新的化学工具，用于有效合成生物活性化合物。本研究开发的新方法侧重于利用炔酮高效构建复杂的环状化合物。炔酮是碳碳三键（炔）与碳氧双键（羰基）相连的物质。这种连接增强了双分子加成反应中的化学反应活性。本研究开发的新策略通过生成与生物相关的化合物文库，在药物合成和医学领域得到了应用。作为该项目的教育部分，Chalifoux教授制定了一个外展计划，重点是指导来自低收入，第一代大学家庭的初高中学生以及在科学领域代表性不足的群体。该项目与内华达州里诺地区的中学和高中建立了联系。在Chalifoux集团的研究项目中，来访的高中学生与研究生和本科化学学生密切合作，参与与科学相关的活动。本课题主要研究炔和炔酮的环化和环加成反应。本研究开发了一种操作简单的合成方法，将现成的炔、二炔和二烯起始材料转化为复杂的环和多环靶分子。简单的共轭炔和更复杂的共轭和交叉共轭多炔被探索作为Diels-Alder环加成反应的底物。这些在多组分/串联环化反应中得到进一步阐述，这些反应旨在在一个反应步骤中产生多个新的碳-碳键和环，具有区域和立体化学控制。该研究通过快速生成与生物相关的化合物文库，在药物合成和医学领域具有广泛的应用。除了在初中和高中的活动外，CAREER奖还支持内华达大学的暑期研究活动。这改善了代表性不足的学生进入科学、技术、工程和数学（STEM）职业的招聘，并增加了科学专业学生的留用率。

With this CAREER Award, the Synthesis Program supports the research of Professor Wesley A. Chalifoux of the University of Nevada, Reno. Professor Chalifoux develops new chemical tools for the efficient synthesis of biologically active compounds. New methodology developed in this research focuses on the application of ynones for the efficient construction of complex cyclic compounds. Ynones are substances in which a carbon-carbon triple bond (an alkyne) is connected to a carbon oxygen double bond (a carbonyl group). This connection enhances chemical reactivity in bimolecular addition reactions. New strategies which are developed in this research have applications in the area of pharmaceutical synthesis and the field of medicine through the generation of biologically-relevant compound libraries. As the educational component of this project, Professor Chalifoux develops an outreach program that focuses on the mentoring of middle and high school students from low-income, first-generation college families as well as groups that are underrepresented in science. The project builds connections with middle and high schools located in the Reno, Nevada area. Visiting high school students work closely with graduate and undergraduate chemistry students in science-related activities associated with research projects within the Chalifoux group. In this project, cyclization and cycloaddition reactions of alkynes and alkynones are explored. This research develops an operationally simple synthetic methodology that converts readily available alkyne, diyne and diene starting materials into complex cyclic and polycyclic target molecules. Simple conjugated alkynes and more complex conjugated and cross-conjugated polyynes are explored as substrates for Diels-Alder cycloaddition reactions. These are further elaborated in multicomponent/tandem cyclization reactions that are designed to generate multiple new carbon-carbon bonds and rings in a single reaction step, with regio- and stereochemical control. This research has broad applications in the area of pharmaceutical synthesis and the field of medicine through the rapid generation of biologically relevant compound libraries. In addition to activities at the middle and high schools, the CAREER Award supports summer research activities at the University of Nevada. This improves recruitment of underrepresented students into Science, Technology, Engineering and Mathematical (STEM) careers and increases retention of students in the sciences.