One-Pot Synthesis of Hydroxylated Alkaloids from Sugars via a Pictet–Spengler-Type Reaction
Likai Zhou,
Na Ma,
Jilai Wu,
Weilin Yang,
Lijing Feng,
Song Xie,
Lili Wang,
Hua Chen
Affiliations
Likai Zhou
Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Material Science, Hebei University, Baoding 071002, China
Na Ma
Asset Management Co., Ltd., Hebei University, Baoding 071002, China
Jilai Wu
Comprehensive Experimental Center, Hebei University, Baoding 071002, China
Weilin Yang
Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Material Science, Hebei University, Baoding 071002, China
Lijing Feng
Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Material Science, Hebei University, Baoding 071002, China
Song Xie
Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Material Science, Hebei University, Baoding 071002, China
Lili Wang
Functional Polymer Materials R&D and Engineering Application Technology Innovation Center of Hebei, College of Chemical Engineering and Biotechnology, Xingtai University, Xingtai 054001, China
Hua Chen
Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Material Science, Hebei University, Baoding 071002, China
An efficient and convenient strategy has been successfully developed for the preparation of novel hydroxylated alkaloid derivatives (also called fused multicyclic iminosugars) from p-toluenesulfonylated sugars through a Pictet–Spengler-type mechanism. This method is highly stereoselective, does not require metal catalysts, and capable of conducting gram level reactions (with a 53% yield). Some of such iminosugars had an intermediate antiproliferative effect on HCT116 tumor cells.
