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）：以创新的主要重点，该计划的主要目标是开发高效，完全立体控制和实用的合成策略，以利用易于使用的硅环平台进行复杂的生物活性目标。通过对映选择性对称性化组装，Silacyclopentanes和Silacyclohexanes为许多具有生物医学意义的自然产物中发现的一系列合成有价值的构件提供了新的条目。此外，适当功能化的硅环脚架将导致广泛合成效用的新型不对称催化剂。在拟议的四年赠款期内，我们将集中于以下特定目标：（a）利用功能化五元和六元的硅烷的新立体选择性转换的发展； （b）设计对Nystatin A1的高度收敛合成的设计； （c）开发Neodysiherbaine A的完全立体控制的合成； （d）开发前往PF1018的路线； （e）基于手性硅的刘易斯酸催化剂的合理设计。在广泛的初步结果的支持下，这项全面的研究计划旨在通过创新和有效地利用新型的硅乳模板来推进现代有机合成的最新作品。