Synthesis and Structure Elucidation of Tedanolide C

Tedanolide C 的合成及结构解析

• 批准号: 397946801
• 负责人: Professor Dr. Markus Kalesse
• 金额: --
• 依托单位: Institut für Organische Chemie
• 依托单位国家: 德国
• 项目类别: Research Grants
• 财政年份: 2017
• 资助国家: 德国
• 起止时间: 2016-12-31 至 2021-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/397946801?language=en
• 关键词: Synthesis; Structure; Elucidation; Tedanolide

This projects aims at the total synthesis of tedanolide C. Tedanolid C exhibits, compared to the other tedanolides, a much higher oxidation pattern which leads to a tertiary hydroxyl group next to a primary alcohol. These features represent a particular synthetic challenge for the construction of this very fragment but also for the assembly of all building blocks. We developed a variation of the Kiyooka aldol reaction, which was used by us for the generation of this complex fragment. Within this proposal we delineate how tedanolide C can be constructed using our Kiyooka aldol approach. A total synthesis of tedanolide C would have significance since several groups question the proposed configuration and a successful total synthesis would confirm one or the other structural proposal. Tedanolide C as well as the whole family of tedanolides represent an important class of natural products as they address to distinct binding sites at the ribosome and belong to one of the most cytotoxic natural products. The fact that these are marine natural products disables access through fermentation and makes a synthetic access even more important.

本项目旨在全合成替丹酮C。与其他替丹内酯相比，替丹内酯C表现出高得多的氧化模式，这导致在伯醇旁边产生叔羟基。这些特征代表了构建这个片段以及组装所有构建模块的特定合成挑战。我们开发了一种变化的清冈羟醛缩合反应，这是由我们用于生成这个复杂的片段。在这个建议中，我们描绘了如何tedanarc可以使用我们的清冈醛方法构建。tedanlavin C的全合成将具有重要意义，因为几个小组质疑所提出的构型，并且成功的全合成将证实一种或另一种结构建议。替旦醇C以及整个替旦内酯家族代表一类重要的天然产物，因为它们针对核糖体上的不同结合位点，并且属于最具细胞毒性的天然产物之一。事实上，这些是海洋天然产品，无法通过发酵获得，使合成获得变得更加重要。