Login / Signup

Electrooxidative tricyclic 6-7-6 fused-system domino assembly to allocolchicines by a removable radical strategy.

Yan ZhangChanchan MaZhenzhi CaiJulia StruweShengjie ChenJinming XuShiyin LiWangyu ZengHarry L Anderson
Published in: Green chemistry : an international journal and green chemistry resource : GC (2022)
Natural allocolchicine and analogues derived thereof a tricyclic 6-7-6-system have been found as key scaffold of various biologically relevant molecules. However, the direct preparation of the allocolchicine motif remains difficult to date. Herein, we report on an electrooxidative radical cyclization of biarylynones with various carbon- and heteroatom-centered radical precursors via a sequential radical addition/7- endo-trig /radical cyclization domino reaction. This approach provides a step-economical and strategically novel disconnection for the facile assembly of a wide range of carbocyclic 6-7-6 fused ring systems. Remarkably, the sulfonyl group on the products could be easily removed by photocatalysis at room temperature with high yields.
Keyphrases
  • room temperature
  • ionic liquid
  • mass spectrometry
  • molecular dynamics simulations
  • molecularly imprinted
  • highly efficient
  • simultaneous determination
  • structure activity relationship