NMR, Computation and Total Synthesis; Uncovering the Stereochemistry of 1,5-polyol-containing Macrolides

核磁共振、计算和全合成；

• 批准号: 2625066
• 金额: --
• 依托单位: University of Bristol
• 依托单位国家: 英国
• 项目类别: Studentship
• 财政年份: 2021
• 资助国家: 英国
• 起止时间: 2021 至 无数据
• 项目状态: 未结题
• 来源: https://gtr.ukri.org/projects?ref=studentship-2625066
• 关键词: NMR; Computation; Total; Synthesis; Uncovering

Amantelide A is one of a group of polyhydroxylated macrolide natural products furnished with a repeated sequence of 1,5-related stereogenic centers. Such 1,5-polyol motifs represent a significant challenge for their synthesis, NMR and computational analyses, as the remote position of the stereocenters can complicate these elements. This project aims to develop a general procedure for assigning the stereochemical configuration of highly furnished polyhydroxylated molecules with distal stereocenters. More broadly we aim to 'fingerprint' such molecules in such a way as to derive the configurational relationships between contiguous stereocenters without the explicit need to synthesise their parent compounds. A synergistic approach combining the efficient and stereoselective synthetic methodologies developed within the Aggarwal group with the advanced NMR and computational analyses of the Butts group could afford a reliable methodology for uncovering the stereochemistry otherwise challenging macrocyclic compounds.

Amantelide A是一组具有1,5相关立体中心重复序列的多羟基大环内酯类天然产物。这些1,5-多元醇基序对于它们的合成、核磁共振和计算分析来说是一个重大的挑战，因为立体中心的遥远位置会使这些元素复杂化。本项目旨在开发一种通用程序，用于分配具有远端立体中心的高度提供的多羟基化分子的立体化学构型。更广泛地说，我们的目标是“指纹”这样的分子，以这样一种方式推导出连续立体中心之间的构型关系，而不需要明确地合成它们的母体化合物。将Aggarwal团队开发的高效立体选择性合成方法与Butts团队先进的核磁共振和计算分析相结合的协同方法，可以为揭示立体化学方面具有挑战性的大环化合物提供可靠的方法。