Asymmetric Total Synthesis and Absolute Configuration Determination of (-)-Verrupyrroloindoline

【作者】 Zhi-Ping Yang； Qian He； 叶剑良； Pei-Qiang Huang；

【Author】 Zhi-Ping Yang;Qian He;Jian-Liang Ye;Pei-Qiang Huang;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;State Key Laboratory of Applied Organic Chemistry, Lanzhou University;

【机构】 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； State Key Laboratory of Applied Organic Chemistry, Lanzhou University；

【摘要】 <正>The first asymmetric total synthesis of(-)-verrupyrroloindoline(20% overall yield in 6 steps) is described. The short approach was enabled by Buchwald’s Cu(I)-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(3) was able to be determined as 7 R,10 R,11 R by X-ray diffraction [Flack parameter x(μ) = 0.04(7)] of the intermediate 2, which made up of atoms no heavier than Si.更多还原