New Cycloaddition and Annulation Strategies for Organic Synthesis

在这项由化学系化学合成计划支持的项目中，麻省理工学院化学系的Rick L.Danheiser教授将开发基于环化合成环状有机分子的新方法。碳环和杂环系统经常存在于生物重要化合物的结构中，包括那些在医学和农业中有应用的化合物。这类化合物还可用于材料化学或电子应用。因此，开发新的合成方法，既简化又补充更传统的方法，具有广泛的科学意义。所开发的合成方法将为学术界和工业界的研究人员提供合成此类重要杂环化合物的新工具。该计划资助的研究生将接受培训，以发展他们作为合成化学家的技能，并发展他们的口头和书面交流技能。这些研究生还将担任麻省理工学院新英格兰地区高中外展计划的协调员，该计划的一个重要组成部分是接触在STEM学科中传统上代表性较低的群体的成员。合成经常被描述为化学的“使能技术”。周环反应作为这项研究的主要载体，主要致力于设计基于周环反应级联的收敛苯环策略。这项拟议研究的一个主要特点是以应变和不寻常的分子为基础的化学为基础开发新的合成反应。这些新方法将被应用于提供快速获得高取代杂环体系的途径，包括吲哚和吡啶。

In this project supported by the Chemical Synthesis Program of the Chemistry Division, Professor Rick L. Danheiser of the Department of Chemistry at the Massachusetts Institute of Technology will develop new methods for the "annulation-based" synthesis of cyclic organic molecules. Carbocyclic and heterocyclic ring systems are often found in the structures of biologically important compounds, including those with applications in medicine and agriculture. Such compounds also are of interest for materials chemistry or electronics applications. Therefore, the development of new methods for their synthesis that are both streamlined and complementary to more traditional methods, is of broad scientific interest. The synthetic methods developed in the proposed research will provide researchers in both academia and industry with new tools for the synthesis of such important heterocyclic compounds. The graduate students supported under this program will receive training to develop their skills as synthetic chemists, and to develop their oral and written communication skills. The graduate students will also serve as coordinators for the MIT Outreach Program to high schools in the New England region an important component of which is directed at reaching out to members of groups traditionallys underrepresented in the STEM disciplines.Synthesis is often described as the "enabling technology" of chemistry. Pericyclic reactions serve as the primary vehicle to be exploited in this research, with most efforts focused on the design of convergent benzannulation strategies based on cascades of pericyclic reactions. A key feature of the proposed research is the development of new synthetic reactions based on the chemistry of strained and unusual molecules as building blocks. The new methods will be applied to provide rapid access to highly substituted heterocyclic systems including indoles and pyridines.