New Cycloaddition and Annulation Strategies for Organic Synthesis

本研究由化学系化学合成项目资助，马萨诸塞州理工学院化学系的丹海泽将开发新的方法，用于环状有机分子的“基于环化的”合成。 碳环和杂环系统通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应用的化合物。这些化合物也对材料化学或电子应用感兴趣。 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。 在拟议的研究中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。 该计划支持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沟通技巧。 研究生还将担任麻省理工学院外展计划的协调员，以新英格兰地区的高中，其中一个重要组成部分是针对接触传统上在STEM学科中代表性不足的群体的成员。合成通常被描述为化学的“使能技术”。 周环反应作为主要的车辆被利用在这项研究中，与大多数的努力集中在设计的收敛benzannulation策略的基础上级联的周环反应。 拟议研究的一个关键特征是开发基于应变和不寻常分子化学的新合成反应。 新方法将用于提供快速获得高度取代的杂环系统，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.