Department of Applied Chemistry, Faculty of Science and Engineering , Waseda University 3-4-1 Ohkubo , Shinjuku-ku, Tokyo 169-8555 , Japan.
J Org Chem. 2018 Jul 6;83(13):7010-7018. doi: 10.1021/acs.joc.7b02997. Epub 2018 Feb 1.
Total synthesis and structural determination of XR774 has been accomplished. The benzo[ j]fluoranthene skeleton has been constructed by regioselective coupling between tetraline 3 and tetralone 4 successively followed by the sequential transformation including the Birch reduction to prepare allylic alcohol, simultaneous bromination of vinylic and aromatic moieties, and the nickel-mediated intramolecular coupling reaction. The optical resolution of racemic 17 led to the first total synthesis of (-)-XR774.
已完成 XR774 的全合成和结构确定。苯并[j]荧蒽骨架通过 3 位和 4 位的区域选择性偶联，随后进行一系列转化，包括伯奇还原制备烯丙醇、乙烯基和芳基同时溴化以及镍介导的分子内偶联反应，成功构建。通过外消旋 17 的光学拆分，首次完成了（-）-XR774 的全合成。
