Total synthesis of (±)-vinoxine: construction of the bridged pyrido[1,2-a]indole skeleton via Tf2O-mediated Bischler-Napieralski reaction and stereoselective radical cyclization
Total synthesis of (±)-vinoxine: construction of the bridged pyrido[1,2-a]indole skeleton via Tf2O-mediated Bischler-Napieralski reaction and stereoselective radical cyclization
复制标题
(±)-vinoxine 的全合成：通过 Tf2O 介导的 Bischler-Napieralski 反应和立体选择性自由基环化构建桥联吡啶并[1,2-a]吲哚骨架
DOI：
10.1039/d2ob00274d
复制
发表时间：
2022
影响因子：
3.2
通讯作者：
Tokuyama Hidetoshi
中科院分区：
文献类型：
--
作者：
Okada Kosuke;Ueda Hirofumi;Tokuyama Hidetoshi
通过Tf 2 O介导的Bischler-Napieralski反应，实现了多取代四氢吡啶并[1，2-a]吲哚骨架的全合成。基于C3位的一个立体化学，通过自由基环化立体选择性地构建了特征性的二氮杂双环[3.3.1]壬烷骨架。所建立的方法学为含多取代吡啶并[1，2-a]吲哚骨架的天然产物和药物的合成提供了新的选择。
The total synthesis of (±)-vinoxine was achieved featuring the assembly of a multi-substituted tetrahydropyrido[1,2-a]indole skeleton through the Tf2O-mediated Bischler–Napieralski reaction. The characteristic diazabicyclo[3.3.1]nonane skeleton was stereoselectively constructed via radical cyclization based on the one stereochemistry of the C3 position. The established methodology provides new options for the synthesis of natural products and pharmaceuticals containing the multi-substituted pyrido[1,2-a]indole skeleton.