（+）-冠状脂肪酸的可扩展合成。
A scalable synthesis of (+)-coronafacic acid.
机构信息
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, Japan.
Department of Molecular and Chemical Life Sciences, Graduate School of Life Sciences, Tohoku University, Sendai, Japan.
出版信息
Chirality. 2020 Apr;32(4):423-430. doi: 10.1002/chir.23172. Epub 2020 Jan 30.
A facile, efficient, and scalable synthesis of optically pure coronafacic acid by resolution of racemic coronafacic acid obtained using an improved version of Watson's method has been developed. By optimizing the boron-mediated aldol reaction of Watson, we were able to prepare 2.1 g of racemic coronafacic acid. This was coupled with (S)-4-isopropyl-2-oxazolidinone to give a mixture of diastereomeric coronafacyl oxazolidinones, which were readily separable by silica-gel column chromatography to give 630 mg of optically pure (+)-coronafacic acid.
已开发出一种通过拆分使用 Watson 方法的改进版本获得的外消旋 coronafacic 酸来简便、高效且可规模化合成光学纯 coronafacic 酸的方法。通过优化 Watson 的硼介导的Aldol 反应，我们能够制备 2.1 g 的外消旋 coronafacic 酸。然后，将其与（S）-4-异丙基-2-恶唑烷酮偶联，得到非对映异构体混合物的 coronafacyl 恶唑烷酮，通过硅胶柱色谱法很容易将其分离，得到 630 mg 的光学纯（+）-coronafacic 酸。
Zotero 插件