New Silacyclic Platforms for Complex Target Synthesis

用于复杂目标合成的新型硅环平台

• 批准号: 6681354
• 负责人: SERGEY A KOZMIN
• 金额: $ 23.92万
• 依托单位: UNIVERSITY OF CHICAGO
• 依托单位国家: 美国
• 财政年份: 2003
• 资助国家: 美国
• 起止时间: 2003-06-01 至 2007-05-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/6681354
• 关键词: alkaloids; catalyst; chemical synthesis; cyclic compound; cyclohexanes; cyclopentane; excitatory aminoacid; nystatin; silanes; silicon compounds; stereochemistry

DESCRIPTION (provided by applicant): With the main emphasis on innovation, the primary objective of this program is to develop highly efficient, fully stereocontrolled, and practical synthetic strategies to complex bioactive targets utilizing readily available silacyclic platforms. Assembled via enantioselective desymmetrization, silacyclopentanes and silacyclohexanes provide new entries into a range of synthetically valuable building blocks found in many natural products of biomedical significance. In addition, appropriately functionalized silacyclic scaffolds will lead to new classes of asymmetric catalysts of broad synthetic utility. Within the proposed four-year grant period, we will concentrate on the following specific objectives: (a) development of new stereoselective transformations utilizing functionalized five- and six-membered silanes; (b) design of a highly convergent synthesis of nystatin A1; (c) development of a fully stereocontrolled synthesis of neodysiherbaine A; (d) development of expeditious route to PF1018; (e) rational design of chiral silicon-based Lewis acid catalysts. Supported by extensive preliminary results, this comprehensive research program is aimed at advancing the state-of-the-art of modern organic synthesis through innovative and efficient use of novel silacycles templates.

描述（由申请人提供）：该计划的主要重点是创新，其主要目标是开发高效，完全立体控制和实用的合成策略，以利用现成的硅杂环平台合成生物活性靶标。通过对映体选择性去对称化组装，硅杂环戊烷和硅杂环己烷提供了一系列在许多具有生物医学意义的天然产物中发现的合成有价值的结构单元的新条目。此外，适当官能化的硅杂环支架将导致广泛的合成用途的新类别的不对称催化剂。在拟议的四年资助期内，我们将集中于以下具体目标：（a）利用官能化五元和六元硅烷开发新的立体选择性转化;（B）设计高度收敛的制霉菌素A1合成方法;（c）开发完全立体控制的合成neodysiherbaine A的方法;（d）开发快速合成PF 1018的路线;（e）开发新的合成方法。（e）手性硅基刘易斯酸催化剂的合理设计。在广泛的初步结果的支持下，这个综合性的研究计划旨在通过创新和有效地使用新型硅杂环模板来推进现代有机合成的最新发展。