Direct Synthesis of cis-Bicyclic γ-Lactam Derivatives from Iminosugar C-Coumarinyl Glycosides
Likai Zhou1,2, Lijing Feng1, Jilai Wu3
1Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Materials Science, Hebei University, Baoding, Hebei 071002, P. R. China.
Abstract:
A simple and effective synthesis method has been developed through Mannich and transannular reaction mechanisms to convert iminosugar C-coumarinyl glycosides 4a into cis-bicyclic γ-lactam derivatives 8a. The adaptability of this method has been demonstrated through various substituted coumarins, tosylated sugars, and amines. The extension reaction proved the plasticity of the bicyclic skeleton. In addition, this reaction has the characteristics of simple operation, a high yield, and high atomic economy.
Related Concept Videos
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
β-Dicarbonyl Compounds via Crossed Claisen Condensations
Cycloaddition Reactions: Overview
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...


