Total Synthesis of Communesin B

Communesin B 的全合成

• 批准号: 7108887
• 负责人: JIMMY WU
• 金额: $ 4.4万
• 依托单位: STANFORD UNIVERSITY
• 依托单位国家: 美国
• 财政年份: 2006
• 资助国家: 美国
• 起止时间: 2006-02-28 至 2008-02-27
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/7108887
• 关键词: alkaloids; biological products; cytotoxicity; drug design /synthesis /production; heterocyclic polycyclic compound; postdoctoral investigator

DESCRIPTION (provided by applicant): The specific goal of this research proposal is the total synthesis of the indoline alkaloid communesin B. Communesin B is a broadly biologically active natural product that posseses two vicinal quaternary centers and two aminal moeities embedded within a heptacyclic framework. There have been no reported total syntheses to date. The successful synthesis of this compound would represent an important advance in the field of alkaloid synthesis. The key step in the synthesis of communesin B would be a Mo-, Ir-, or W- catalyzed asymmetric allylic alkylation (AAA) reaction which will employ indole derivatives as the nucleophile. The use of indoles nucleophiles in the AAA reaction has not been precedented and would be a significant extension of the current AAA technology.

描述(申请人提供)：本研究方案的具体目标是全合成吲哚生物碱Commesin B。Commesin B是一种具有广泛生物活性的天然产品，具有两个邻近的四元中心和两个嵌入在七环框架中的氨基酸基团。到目前为止，还没有关于全合成的报道。该化合物的成功合成将代表着生物碱合成领域的重要进展。香豆素B合成的关键步骤是Mo、Ir或W催化的不对称烯丙基烷基化(AAA)反应，该反应将使用吲哚类化合物作为亲核剂。在AAA反应中使用吲哚亲核试剂还没有先例，这将是当前AAA技术的重大扩展。