Department of Chemistry, Fujian Provincial Key Laboratory of Chemical Biology, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), College of Chemistry and Chemical Engineering , Xiamen University , Xiamen , Fujian 361005 , P. R. China.
State Key Laboratory of Applied Organic Chemistry , Lanzhou University , Lanzhou 730000 , P. R. China.
Org Lett. 2018 Jul 20;20(14):4200-4203. doi: 10.1021/acs.orglett.8b01579. Epub 2018 Jul 3.
The first asymmetric total synthesis of (-)-verrupyrroloindoline (20% overall yield in 6 steps) is described. The short approach was enabled by Buchwald's Cu(II)-catalyzed asymmetric conjugate reduction, DMDO-triggered one-pot four-step tandem reaction, and the first amide-selective Ir-catalyzed direct reduction of β-carboethoxy tertiary lactam. Along with the total synthesis, the absolute configuration of natural verrupyrroloindoline was determined as 7 R,10 R,11 R.
本文描述了（-）-verrupyrroloindoline 的首次不对称全合成（总收率为 6 步中的 20%）。该短路线的实现得益于 Buchwald 的 Cu(II)催化不对称共轭还原、DMDO 触发的一锅四步串联反应，以及首次酰胺选择性 Ir 催化β-羰乙酯叔内酰胺的直接还原。通过全合成，确定了天然 verrupyrroloindoline 的绝对构型为 7R,10R,11R。
