Department of Chemistry, Northwestern University , 2145 Sheridan Road, Evanston, Illinois 60208, United States.
J Am Chem Soc. 2014 Dec 24;136(51):17750-6. doi: 10.1021/ja5109694. Epub 2014 Dec 11.
The enantioselective synthesis of maoecrystal V, a cytotoxic polycyclic diterpene, is described. Key reactions in the synthesis include an intramolecular Heck reaction, an oxidative cycloetherification, and an intermolecular Diels-Alder reaction to forge the carbocyclic core in a concise and stereoselective manner. Late-stage amine and C-H oxidation is used to install the final functional groups required to complete the synthesis.
描述了马兜铃酮 V 的对映选择性合成,马兜铃酮 V 是一种具有细胞毒性的多环二萜。合成中的关键反应包括分子内 Heck 反应、氧化环醚化反应和分子间 Diels-Alder 反应,以简洁和立体选择性的方式构建碳环核心。晚期的胺和 C-H 氧化用于安装完成合成所需的最后官能团。