One-Pot Stereoselective Synthesis of Different Fused Multicyclic Iminosugars Based on the Iminium-lon Intermediate  

作　　者：Song Xie Jilai Wu Likai Zhou Chao Wei Xiaoliu Li Hua Chen 

机构地区：[1]Key Laboratoryof Chemical Biology of Hebei Province,College of Chemistry and Material Science,Hebei University,Baoding,Hebei 071002,China [2]College of Chemistry and Chemical Engineering,Xingtai University,Xingtai,Hebei 054001,China

出　　处：《Chinese Journal of Chemistry》2024年第2期142-150,共9页中国化学（英文版）

基　　金：supported by the National Natural Science Foundation of China(NSFC)(21772031);the Natural Science Foundations of Hebei Province(B2019201398).

摘　　要：Different novel fused multicyclic iminosugars were synthesized from D-ribose tosylate,aniline and vinyl ethyl ether by one-pot three-component stereoselective[4+2]reaction at different temperatures.The iminium-ion is the key intermediate for the reaction.As a result,several complex fused iminosugars 3a were obtained by aza-Diels-Alder mechanism at 60℃,while a series of aza-C-glycosides 5a were prepared by Mannich reaction at room temperature accompanied by another tetrahydroquinoline-fused iminosugars 4a(tricyclic derivatives)through aza-Diels-Alder cycloaddition.This strategy will help to construct structurally diverse and bioactive iminosugar analogues.

关 键 词：Fused multicyclic iminosugar Aza-Diels-Alder cycloaddition Mannich reaction TETRAHYDROQUINOLINE Multicomponent reactions Enantioselectivity Cyclization 

分 类 号：O62[理学—有机化学]