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.

项目总结/摘要 小分子的化学合成仍然是一个重要的研究领域。这种努力可以导致 开发新的和改进的方法，提供有趣或重要的支架， 提供反应性和合成设计的基本见解，反过来，可以使未来的研究 努力该方案的重点是实现复杂分子十二面体烷的全合成 通过发展碳-碳键形成反应级联。在目标1中，二聚体的藜芦基支架 将被制备并用于烯烃复分解异构化反应。这一奋进将提供访问 一种后期中间体，同时能够研究和开发烯烃的独特变体 分子复杂性组装的方法论。在目标2中，对称的五烯底物将是 合成并用于一个独特的和雄心勃勃的多烯环化，涉及所有五个烯烃，以获得 在最后的合成步骤中使用十二烷。