One-Pot Synthesis of Hydroxylated Alkaloids from Sugars via a Pictet–Spengler-Type Reaction

Abstract

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.

Keywords

• hydroxylated alkaloids
• fused multicyclic iminosugars
• Pictet–Spengler reaction
• antitumor activity