Hydrocarbon Oxidation Methods for Synthesis

烃氧化合成方法

• 批准号: 8337059
• 负责人: Maria White
• 金额: $ 29.19万
• 依托单位: UNIVERSITY OF ILLINOIS AT URBANA-CHAMPAIGN
• 依托单位国家: 美国
• 财政年份: 2006
• 资助国家: 美国
• 起止时间: 2006-09-26 至 2016-08-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/8337059
• 关键词: Acids; Alkenes; Alkylation; Amino Alcohols; Area; Base Pairing; Biological; Biological Factors; Carbon; Catalysis; Chemicals; Chemistry; Complex; Coupling; Development; Diamines; Future; Glycols; Goals; Hydrocarbons; Hydrogen Bonding; Lead; Ligands; Methods; Molecular; Nature; Nitrogen; Oxidants; Oxygen; Pathway interactions; Pharmacologic Substance; Process; Property; Quinones; Reaction; Research; Skeleton; Sulfoxide; System; Therapeutic; Time; base; catalyst; flexibility; functional group; improved; novel; oxidation; rapid technique; scaffold; tool; wasting

DESCRIPTION (provided by applicant): The architectural and functional group complexity of natural products often confers to them unique modes of biological activity and significant therapeutic value. Despite transformative advances in catalytic methods and strategies for constructing highly complex molecules, the practice of total synthesis still remains a laborious and time intensive pursuit. Consequently, such compounds are rarely sought or evaluated as potential therapeutics. Historically, the development of new synthetic methods has had a profound impact on the efficiency of complex molecule synthesis. New reaction classes that lead to fundamentally novel reactivity stand to promote the largest advances in this regard. As a guide, we can look towards Nature¿s synthetic strategies that systematically employ C-H oxidation and complexity generating C-C bond forming reactions. This proposal seeks to establish allylic C-H bonds as a new functional group for widespread use in complex molecule synthesis. To achieve this goal we will exploit a highly versatile ¿-allyPd intermediate, accessed through allylic C-H cleavage, and develop general strategies by which it can participate in diverse reaction types with consistently high selectivities. Collectively, we expect these Pd(II)-catalyzed allylic C-H functionalization reactions to become fundamental tools for streamlining the synthesis of important structural motifs found in natural products, bioactive compounds, and medicinal agents. Moreover, the general principles that emerge from this approach will be broadly applicable to the field of C-H activation.) PUBLIC HEALTH RELEVANCE: The objective of this research is to discover and develop catalytic reactions that establish the allylic C- H bond as a new functional group for widespread use in the synthesis of structural motifs found in natural products, bioactive compounds, and medicinal agents.)

描述（由申请人提供）：天然产物的结构和功能组复杂性通常赋予它们独特的生物活性模式和显著的治疗价值。尽管在构建高度复杂分子的催化方法和策略方面取得了变革性的进展，但全合成的实践仍然是一个费力和耗时的追求。因此，很少寻求或评估此类化合物作为潜在的治疗方法。 从历史上看，新合成方法的发展对复杂分子合成的效率产生了深远的影响。新的反应类别，导致从根本上新颖的反应性站在促进这方面的最大进步。作为指导，我们可以看看自然的合成策略，系统地采用C-H氧化和复杂性产生C-C键形成反应。这一建议旨在建立烯丙基C-H键作为一个新的功能基团，在复杂的分子合成中广泛使用。为了实现这一目标，我们将利用一个高度通用的<$-allyPd中间体，通过烯丙基C-H裂解访问，并制定通用策略，通过它可以参与不同的反应类型，始终具有高选择性。 总的来说，我们期望这些Pd（II）催化的烯丙基C-H官能化反应成为简化天然产物，生物活性化合物和药物中发现的重要结构基序的合成的基本工具。此外，这种方法产生的一般原理将广泛适用于C-H活化领域。 公共卫生关系：本研究的目的是发现和发展催化反应，建立烯丙基C-H键作为一个新的官能团，广泛用于合成天然产物，生物活性化合物和药物中发现的结构基序。