New Cycloaddition and Annulation Strategies for Organic Synthesis

在这个由化学部化学合成项目支持的项目中，麻省理工学院化学系的Rick L. Danheiser教授将开发“环基”合成环状有机分子的新方法。碳环和杂环系统经常在重要的生物化合物的结构中发现，包括那些在医学和农业中应用的化合物。这类化合物在材料化学或电子学应用中也很有价值。因此，开发新的合成方法，既精简又补充更传统的方法，具有广泛的科学兴趣。本研究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沟通能力。研究生还将担任麻省理工学院新英格兰地区高中外展项目的协调员，这是该项目的重要组成部分，旨在接触传统上在STEM学科中代表性不足的群体成员。合成通常被描述为化学的“使能技术”。在本研究中，周环反应是主要的载体，大部分的努力都集中在基于周环反应级联的收敛苄基化策略的设计上。提出的研究的一个关键特征是基于张力和不寻常分子的化学作为构建块的新合成反应的发展。新方法将用于提供快速获取高取代杂环系统，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.