A Claisen-Sakurai Strategy to Highly Substituted Cyclopentenols: Applications to the Syntheses of Echinopine A and B

高取代环戊烯醇的 Claisen-Sakurai 策略：在 Echinopine A 和 B 合成中的应用

• 批准号: EP/I006605/1
• 负责人: Matthew Cook
• 金额: $ 12.85万
• 依托单位: Queen's University Belfast
• 依托单位国家: 英国
• 项目类别: Research Grant
• 财政年份: 2010
• 资助国家: 英国
• 起止时间: 2010 至 无数据
• 项目状态: 已结题
• 来源: https://gtr.ukri.org/projects?ref=EP%2FI006605%2F1
• 关键词: Claisen; Sakurai; Strategy; Highly; Substituted

The development of new synthetic method is key to the evolution of organic chemistry. In particular new methods that can produce molecules with dense functionality in just a few steps is a shared goal. We are proposing combining two well know reactions (the Claisen rearrangement and Sakurai allylation) to create a new domino reaction that can produce molecules with complex functionalilty embedded within it in a single transformation. These densly functionalised small molecules could be of use in both the total synthesis of natural products and in the discovery of new pharmaceutical products. With this grant a new way of making complex molecules rapidly will be developed. We hope to apply this to the rapid synthesis of compounds that exhibit potent biological properties, both natural and unnatural. We will embark on a synthesis of echinopinine A and B two complex natural products with novel architectures. Although their biological properties have not been fully elucidated they were isolated from plants known to exhibit many medicinal properties including anti-cancer activity.

新合成方法的发展是有机化学发展的关键。特别是，可以在几个步骤中生产具有密集功能的分子的新方法是一个共同的目标。我们建议结合两个众所周知的反应（克莱森重排和樱井烯丙基化），以创建一个新的多米诺骨牌反应，可以在一个单一的转换中产生嵌入其中的具有复杂功能的分子。这些密集功能化的小分子可用于天然产物的全合成和新药物的发现。有了这笔赠款，一种快速制造复杂分子的新方法将被开发出来。我们希望将其应用于快速合成具有强大生物学特性的化合物，无论是天然的还是非天然的。我们将着手于棘针碱A和B两个复杂的天然产物与新的架构的合成。虽然它们的生物学特性尚未完全阐明，但它们是从已知具有许多药用特性（包括抗癌活性）的植物中分离出来的。