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Updated: Jan 9, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Total Synthesis of (-)-Daphenylline
Bo Xu1,2, Bingyang Wang1,2, Wen Xun1,2
1State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou, 510530, China.
A concise total synthesis of the Daphniphyllum alkaloid (-)-daphenylline was achieved in 19 steps. This study highlights key stereoselective reactions for constructing the complex tetracyclic core and DF ring system.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
Background:
- Daphniphyllum alkaloids are a complex class of natural products.
- (-)-Daphenylline is a significant target molecule within this class.
Purpose of the Study:
- To achieve a concise and highly stereoselective total synthesis of (-)-daphenylline.
- To develop novel synthetic strategies for constructing complex alkaloid structures.
Main Methods:
- Stereoselective Mg(ClO4)2-catalyzed intramolecular amide addition cyclization.
- Intramolecular Diels-Alder reaction for ABCD core construction.
- Robinson annulation and oxidative aromatization.
- Intramolecular Friedel-Crafts cyclization for DF ring installation.
Main Results:
- Successful total synthesis of (-)-daphenylline.
- 19 steps in the longest reaction sequence.
- 7.6% overall yield achieved.
Conclusions:
- The developed synthetic route is efficient and stereoselective.
- This synthesis provides a valuable pathway for accessing Daphniphyllum alkaloids.
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