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Updated: Aug 8, 2025
Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Total Synthesis of (-)-Levesquamide
Yingjun Jiang1, Xiaoyu Liu1, Wenxuan Li1
1State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
The total synthesis of levesquamide, a complex natural product, was achieved for the first time. This study details a novel synthetic route to its unique pyridine-isothiazolinone core structure.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Medicinal Chemistry
Background:
- Levesquamide is a natural product featuring a rare pentasubstituted pyridine-isothiazolinone skeleton.
- The complex structure of levesquamide presents significant synthetic challenges.
Purpose of the Study:
- To achieve the first total synthesis of the natural product levesquamide.
- To develop a novel synthetic strategy for constructing the unique pyridine-isothiazolinone core.
Main Methods:
- The synthesis commenced from kojic acid.
- Key steps included Suzuki coupling, copper-mediated thioether formation, and Pummerer-type cyclization.
Main Results:
- The total synthesis of levesquamide was successfully accomplished.
- A novel pentasubstituted pyridine-isothiazolinone skeleton was constructed.
Conclusions:
- This work provides the first total synthesis of levesquamide.
- The developed synthetic methodology offers a new route to access complex pyridine-isothiazolinone natural products.
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