New Cycloaddition and Annulation Strategies for Organic Synthesis

有机合成的新环加成和成环策略

• 批准号: 1111567
• 负责人: Rick Danheiser
• 金额: $ 43.5万
• 依托单位: Massachusetts Institute of Technology
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2011
• 资助国家: 美国
• 起止时间: 2011-08-01 至 2015-04-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1111567&HistoricalAwards=false
• 关键词: New; Cycloaddition; Annulation; Strategies; Organic

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 efficient synthesis of cyclic organic molecules. The goal of this research program is the development of new strategies with the power to dramatically streamline the synthesis of carbocyclic and heterocyclic organic compounds. 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. In the proposed research, the development of a "tandem strategy" will be investigated in which a vinylketene based benzannulation reaction is employed in conjunction with various heterocyclization processes to provide efficient access to highly substituted polycyclic benzo-fused heterocyclic systems including indoles and carbazoles. The application of this chemistry to the synthesis of the antioxidant alkaloid antiostatin A1, the antifungal antibiotic carbazomycin A, the marine alkaloid herbindole C, the redox cofactor pyrroloquinoline quinone (PQQ), and an electronically interesting pentacyclic heteroaromatic system will be investigated.Carbocyclic and heterocyclic ring systems are incorporated in the structures of numerous biologically important compounds, and the development of highly efficient methods for their synthesis has great value in providing improved access to molecules with important applications in medicine, materials chemistry, and many other areas. Synthesis is often described as the "enabling technology" of chemistry. The synthetic methods developed in the proposed research will provide researchers in both academia and industry with new tools for the synthesis of important heterocyclic compounds with applications in medicine, agriculture, electronics, and other areas. The graduate students supported under this program will receive training to develop their skills as synthetic chemists, and will also receive training in scientific ethics and training to develop their oral and written communication skills. The graduate students will also serve as coordinators for the MIT Outreach Program which each year visits ca. 25 high schools in the New England region providing presentations on chemistry and careers in science. Approximately 1200 high school students attend these presentations each year, with ca. 35% of the students being members of underrepresented minority groups.

在化学部化学合成计划支持的该项目中，马萨诸塞州理工学院化学系的Rick L. Danheiser教授将开发新方法，以有效合成环状有机分子。该研究计划的目的是制定新策略，并有能力显着简化碳环糖和杂环有机化合物的合成。周期性反应是在这项研究中被利用的主要工具，大多数努力都集中在基于生周期反应级联反应的融合苯并苯化策略上。在拟议的研究中，将研究“串联策略”的发展，其中将采用基于乙烯基酮的二苯型反应与各种杂环化过程一起使用，以提供有效替代的多环状苯甲酸苯甲酸苯甲酸苯甲酸苯甲酸苯并粉 - 纤维液的访问权限。这种化学的应用在抗氧化生物碱抗抑制素A1的合成中的应用，抗真菌抗生素carbazomycin A，海洋生物碱除草剂C，氧化还原二氧化碳吡咯喹啉奎因酮（PQQ）和一个有趣的pecencation and Electiccy.petcocacy and.precocacy and percocacy and.杂环环系统纳入了许多具有生物学重要化合物的结构中，并且开发高效的合成方法在提供具有重要应用在医学，材料化学和许多其他领域的重要应用的改善中具有巨大的价值。合成通常被描述为化学的“支持技术”。拟议研究中开发的合成方法将为学术界和行业的研究人员提供新的工具，用于合成重要的杂环化合物，并在医学，农业，电子学和其他领域中应用。根据该计划的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，还将接受科学道德和培训的培训，以发展他们的口头和书面沟通能力。研究生还将作为MIT外展计划的协调员，每年访问CA。新英格兰地区的25所中学提供了有关科学化学和职业的演讲。每年约有1200名高中生参加这些演讲，并与CA一起参加。 35％的学生是代表性不足的少数群体成员。