Total Synthesis of Dodecahedrane via Carbon–Carbon Bond Forming Cascades

通过碳-碳键形成级联全合成十二面体

• 批准号: 10679420
• 负责人: Luca McDermott Catena
• 金额: $ 4.26万
• 依托单位: UNIVERSITY OF CALIFORNIA LOS ANGELES
• 依托单位国家: 美国
• 财政年份: 2023
• 资助国家: 美国
• 起止时间: 2023-07-01 至 2025-06-30
• 项目状态: 未结题
• 来源: https://reporter.nih.gov/project-details/10679420
• 关键词: 3-Dimensional; Alkenes; Area; Basic Science; Biochemistry; Carbon; Chemistry; Complex; Cyclization; Development; Drug Industry; Health; Human; Hydrocarbons; Investigation; Isomerism; Medicine; Methodology; Methods; National Institute of General Medical Sciences; Organic Synthesis; Pentas; Pharmaceutical Preparations; Pharmacologic Substance; Phase; Play; Polyenes; Reaction; Research; Research Support; Role; Route; Site; Training; Validation; Variant; carbon skeleton; chemical synthesis; design; dimer; functional group; fundamental research; human disease; improved; insight; molecular assembly/self assembly; novel; novel therapeutics; pi bond; rapid technique; research study; scaffold; small molecule

Project Summary/Abstract The chemical synthesis of small molecules continues to be a vital area of research. Such efforts can lead to the development of new and improved methods, provide access to interesting or important scaffolds, and provide fundamental insight into reactivity and synthetic design that, in turn, can enable future research endeavors. This proposal is focused on achieving the total synthesis of the complex molecule dodecahedrane via the development of carbon–carbon bond forming reaction cascades. In Aim 1, a dimeric norbornyl scaffold will be prepared and utilized in an olefin metathesis isomerization reaction. This endeavor will provide access to a late-stage intermediate, while enabling the investigation and development of a unique variant of olefin methathesis for the assembly of molecular complexity. In Aim 2, a symmetrical penta-ene substrate will be synthesized and used in a unique and ambitious poly-ene cyclization, involving all five alkenes, to access dodecahedrane in the final synthetic step.

项目摘要/摘要 小分子的化学合成仍然是研究的重要领域。这样的努力可以领导 开发新的和改进的方法，提供有趣或重要的脚手架的访问，以及 提供对反应性和合成设计的基本洞察力，反过来可以使未来的研究 努力。该提议的重点是实现复杂分子十二面体的总合成 通过发展碳 - 碳键形成反应级联的。在AIM 1中，二聚体诺伯基支架 将准备并在烯烃分解异构化反应中制备并使用。这项工作将提供对 后期中级，同时可以投资和开发Olefin的独特变体 用于组装分子复杂性的方法。在AIM 2中，对称的Penta-Ene基板将是 合成并用于独特而雄心勃勃的聚烯环化，涉及所有五种烷烃，以访问 十二面包在最后的合成步骤中。