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

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

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 di...

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Veröffentlicht in:Organic letters 2018-07, Vol.20 (14), p.4200-4203
Hauptverfasser: Yang, Zhi-Ping, He, Qian, Ye, Jian-Liang, Huang, Pei-Qiang
Format: Artikel
Sprache:eng
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Zusammenfassung: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 7R,10R,11R.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b01579