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.

该项目的目的是与其他Tedanolides相比，tedanolide C. tedanolid c展示的总合成，这是一种更高的氧化模式，这会导致二级羟基近代酒精旁边。这些功能代表了构建这个非常碎片的特定综合挑战，也代表了所有构建块的组装。我们开发了一种kiyooka aldol反应的变体，该反应被我们用于生成这种复杂片段。在此提案中，我们描述了如何使用我们的Kiyooka Aldol方法来构建Tedanolide C。 Tedanolide C的总合成将具有重要意义，因为几个小组质疑所提出的配置和成功的总合成将确认一个或另一个结构性建议。 Tedanolide C以及整个Tedanolides家族都代表着重要的天然产物类别，因为它们针对核糖体的独特结合位点，属于最细胞毒性的天然产物之一。这些是海洋天然产品，这一事实可以通过发酵访问访问，并使合成通道变得更加重要。