Total Synthesis of Lytophilippine A

Lytophilippine A的全合成

• 批准号: 174009445
• 负责人: Professor Dr. Martin Hiersemann
• 金额: --
• 依托单位: Forschungsgebiet Organische Chemie
• 依托单位国家: 德国
• 项目类别: Research Grants
• 财政年份: 2010
• 资助国家: 德国
• 起止时间: 2009-12-31 至 2018-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/174009445?language=en
• 关键词: Total; Synthesis; Lytophilippine

The natural product lytophilippine A is a marine polyketide that was isolated from the stinging hydroid Lytocarpus philippinus. The natural product chemistry of the Red Sea hydroid has yet been sparsely investigated. The large number of chiral carbon atoms is the defining and distinguishing element of the molecular architecture of lytophilippine A, and constitutes a significant challenge for asymmetric synthesis. The original proposal for the structure of lytophilippine A was falsified by total synthesis and a revision of the assignment of the absolute configuration is required. Based on our massive experimental groundwork, this project suggests the completion of the total synthesis of the (11R,13R,14R,15R)-configured lytophilippine A and several of its (13,14,15)-diastereomers. With the completion of the total synthesis, we aim to contribute significantly to the final structural assignment and enable further investigation of the biological properties of the natural product. By selecting a target of unusual molecular complexity for our total synthesis research program, we intent to push the frontiers of the science of synthesis to the state of the art and possibly beyond.

天然产物 Lytophilippine A 是一种海洋聚酮化合物，是从刺水螅 Lytocarpus philippinus 中分离出来的。红海水螅的天然产物化学性质尚未得到很少的研究。大量的手性碳原子是 lytophilippine A 分子结构的定义和区别元素，并且对不对称合成构成了重大挑战。最初提出的lytophilippine A 结构被全合成证伪，需要对绝对构型的归属进行修改。基于我们大量的实验基础，该项目建议完成(11R,13R,14R,15R)-构型lytophilippine A及其几种(13,14,15)-非对映体的全合成。随着全合成的完成，我们的目标是为最终的结构分配做出重大贡献，并能够进一步研究天然产物的生物特性。通过为我们的全合成研究计划选择一个异常分子复杂性的目标，我们打算将合成科学的前沿推向最先进的水平，甚至可能超越。

项目成果

Synthesis of a Diastereomer of the Marine Macrolide Lytophilippine A.

海洋大环内酯 Lytophilippine A 非对映异构体的合成

• DOI: 10.1021/acs.orglett.9b00722
• 发表时间: 2019
• 期刊: Organic letters
• 影响因子: 5.2
• 作者: Klüppel;Karayel;Hiersemann
• 通讯作者: Hiersemann