STEREOSELECTIVE SYNTHESIS OF CYCLIC ETHERS

环醚的立体选择性合成

• 批准号: 2701772
• 负责人: P Andrew Evans
• 金额: $ 9.89万
• 依托单位: UNIVERSITY OF DELAWARE
• 依托单位国家: 美国
• 财政年份: 1997
• 资助国家: 美国
• 起止时间: 1997-05-01 至 2002-04-30
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/2701772
• 关键词: acyl group; antifungal agents; chemical synthesis; cyclization; ethers; sesquiterpenes

DESCRIPTION: The aim of the proposal is the application of novel intramolecular acyl radical cyclizations to the synthesis of biologically important cyclic ethers. Although numerous methods exist for the synthesis of these compounds, the search for new methods with increased skeletal and stereochemical flexibility continues. Acyl radicals have received relatively limited attention as reactive intermediates in organic synthesis, despite their potential to efficiently form carbon-carbon bonds. The PI's preliminary synthetic studies indicate that this methodology is likely to have significant utility for target directed synthesis. The synthetic studies proposed herein will focus on the preparation of cis-kumausyne, kumausallene, and the development of a viable strategy for the potent antifungal agents gamberic acids A-D. The gamberic acids A-D represent the most potent antifungal agents known, with activity exceeding that of amphotericin B by over three orders of magnitude, making them extremely important targets.

描述：该提案的目的是应用新的 分子内酰基自由基环化反应合成生物 重要的环醚。 尽管存在许多合成方法， 这些化合物，寻找新的方法，增加骨骼和 立体化学灵活性继续存在。 酰基自由基受到了 作为有机合成中的活性中间体， 尽管它们具有有效形成碳-碳键的潜力。 PI的 初步的综合研究表明，这种方法很可能 对于靶向合成具有重要的实用性。 本文提出的合成研究将集中在制备 顺式库莫炔、库莫萨伦烯，以及制定一项可行的战略， 有效的抗真菌剂gamberic acids A-D。 伽马酸A-D 代表已知最有效的抗真菌剂，其活性超过 使它们的抗菌活性提高了三个数量级， 非常重要的目标。