Total synthesis of (–)-Isodocarpin by a novel nickel-catalyzed decarbonylative reductive cross-coupling

新型镍催化脱羰还原交叉偶联全合成(â)-异杜鹃花碱

• 批准号: 500290506
• 负责人: Dr. Sven Christian Richter
• 金额: --
• 依托单位: Division of Chemistry and Chemical Engineering
• 依托单位国家: 德国
• 项目类别: WBP Fellowship
• 财政年份: 2022
• 资助国家: 德国
• 起止时间: 2021-12-31 至 2022-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/500290506?language=en
• 关键词: Total; synthesis; Isodocarpin; novel; nickel

In this research project, an efficient synthesis of the pharmacologically active and structurally complex natural product (–)-isodocarpin is to be developed. The key steps of the planned convergent synthesis are on the one hand the still to be developed nickel-catalyzed decarbonylative cross-coupling of a carboxylic acid anhydride with a vinyl iodide and on the other hand a photochemically induced radical cyclization to build up the pentacyclic backbone. In addition, the final step of the synthesis requires a selective C–H oxidation of activated positions in the molecule. The target compound (–)-isodocarpin is supposed to be obtained in about 13 steps, while the shortest synthesis to date was completed in 20 steps. This project combines the development of new synthetic methods with the total synthesis of a diterpenoid.

在本研究项目中，将开发具有生物活性和结构复杂的天然产物（-）-isodocarpin的有效合成。计划的收敛合成的关键步骤是一方面仍有待开发的镍催化的脱羰基交叉偶联的羧酸酐与乙烯基碘和另一方面的光化学诱导的自由基环化，以建立五环骨架。此外，合成的最后一步需要分子中活化位置的选择性C-H氧化。目标化合物（-）-异多卡因应该在大约13个步骤中获得，而迄今为止最短的合成在20个步骤中完成。该项目将新合成方法的开发与二萜类化合物的全合成相结合。