Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan.
Faculty of Chemistry, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany.
J Org Chem. 2023 Jun 16;88(12):7674-7683. doi: 10.1021/acs.joc.2c02216. Epub 2023 Jan 26.
We developed an enantioselective synthetic method of constructing a seven-membered ring-fused indole skeleton with contiguous stereocenters for the synthesis of dragmacidin E. Introduction of chirality at the benzylic position was achieved by Ir-catalyzed asymmetric hydrogenation. After construction of the tricyclic molecular framework using Pd-catalyzed cascade cyclization, the tetrasubstituted carbon center was created using the Ag nitrene-mediated C-H amination reaction. The developed method provided access to the functionalized seven-membered ring-fused indole skeleton with a hydroxymethyl branch in the tetrasubstituted carbon.
我们开发了一种对映选择性的合成方法，用于构建具有连续立体中心的七元环稠合吲哚骨架，以合成 dragmacidin E。通过铱催化的不对称氢化在苄位引入手性。使用钯催化的级联环化构建三环分子骨架后，使用银氮宾介导的 C-H 胺化反应形成四取代碳中心。所开发的方法提供了具有四取代碳中羟甲基支链的功能化七元环稠合吲哚骨架的途径。
