Direct Synthesis of <i>cis</i>-Bicyclic γ-Lactam Derivatives from Iminosugar <i>C</i>-Coumarinyl Glycosides
A simple and effective synthesis method has been developed through Mannich and transannular reaction mechanisms to convert iminosugar <i>C</i>-coumarinyl glycosides <b>4a</b> into <i>cis</i>-bicyclic γ-lactam derivatives <b>8a</b>. 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.
Authors
- Chen Hua (ORCID: https://orcid.org/0000-0002-3066-7434)
- Jilai Wu (ORCID: https://orcid.org/0000-0002-8236-0709)
- Likai Zhou
- Chao Wei (ORCID: https://orcid.org/0000-0002-7425-5132)
- Lijing Feng
Institutions
- Comprehensive Clinical Research (US)
- Hebei University (CN)
- Xingtai University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-05-30
- DOI
- https://doi.org/10.1021/acs.orglett.5c01201
- Citations
- 2
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- National Natural Science Foundation of China
- Department of Education of Hebei Province
- Natural Science Foundation of Hebei Province