A facile synthesis of tricyclic skeleton of alkaloid 261C by double [3+2] cycloaddition of pyridinium ylide

作者：Liu, Ruzhang^*; Wang, Xianya; Sun, Jing; Yan, Chao-Guo

来源：Tetrahedron Letters, 2015, 56(48): 6711-6714.

DOI：10.1016/j.tetlet.2015.10.049

• Pyridinium ylide
• Alkaloid 261C
• 1,3-Dipolar cycloaddition
• Pyrrolo[2,1,5-cd]indolizine
• Hammett plot

A facile synthesis of tricyclic skeleton of alkaloid 261C has been achieved by a double [3+2] cycloaddition of p-methoxypyridinium phenacyl bromide and maleimides with high diastereoselectivity. The initial Hammett analysis suggested that the most stable resonance form of pyridinium ylide is the one, the negative charge of which is widely dispersed in the pyridine ring.

• 单位
  扬州大学