School of Life Sciences , Tokyo University of Pharmacy and Life Sciences , 1432-1 Horinouchi , Hachioji , Tokyo 192-0392 , Japan.
Org Lett. 2019 Aug 2;21(15):5813-5816. doi: 10.1021/acs.orglett.9b01776. Epub 2019 Jun 27.
The first enantioselective total synthesis of diocollettines A was accomplished in only six steps from a known compound. A short and practical synthetic route was disclosed, featuring an intensive investigation of the stereoselective aldol reaction as a key step using an easily prepared aldehyde moiety and an enone derivative. The synthetic scheme also includes the efficient stereocontrolled construction of the tricyclic skeleton of diocollettines A by intramolecular acetal formation, stereoselective dihydroxylation, and intramolecular ether cyclization.
从已知化合物出发，仅通过六步就完成了对二乔托灵 A 的首次对映选择性全合成。本文揭示了一条简短而实用的合成路线，其中对关键的立体选择性羟醛缩合反应进行了深入研究，使用了易于制备的醛部分和烯酮衍生物。该合成方案还包括通过分子内环缩醛形成、立体选择性二羟基化和分子内醚环化来高效立体控制地构建二乔托灵 A 的三环骨架。
