Institute of Organic Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 1B, 30167, Hannover, Germany.
Centre of Biomolecular Drug Research (BMWZ), Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 38, 30167, Hannover, Germany.
Chemistry. 2021 Apr 26;27(24):7085-7089. doi: 10.1002/chem.202100553. Epub 2021 Apr 9.
The synthesis of desepoxy-tedanolide C was accomplished and provided experimental evidence on the configuration of tedanolide C. The reported chemical shifts and coupling constants point to a configuration different from the published structure and analogous to the structures of the other members of this family of natural products. The key step is a Kiyooka aldol protocol for the stereoselective synthesis of the tertiary alcohol flanked by three additional oxygenated carbon atoms. Furthermore, two additional aldol reactions and a Julia-Kocienski olefination were used to assemble the carbon framework.
完成了去环氧-泰杜醇 C 的合成，为泰杜醇 C 的结构提供了实验依据。报道的化学位移和偶合常数表明其结构与已发表的结构不同，与该天然产物家族的其他成员的结构类似。关键步骤是通过 Kiyooka 醛醇缩合反应立体选择性合成了三个额外含氧碳原子环绕的叔醇。此外，还使用了另外两个醛醇缩合反应和 Julia-Kocienski 烯烃化反应来组装碳骨架。
