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Total synthesis of (+)-gregatin B and E.
Taichi Kusakabe1, Yasuko Kawai, Keisuke Kato
1Faculty of Pharmaceutical Sciences, Toho University , 2-2-1 Miyama, Funabashi, Chiba, 274-8510, Japan.
Organic Letters
|September 27, 2013
Summary
Researchers achieved the first total synthesis of (+)-gregatin E and a new synthesis of (+)-gregatin B. This work utilized palladium-catalyzed reactions and coupling strategies to construct these complex molecules.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Natural Product Synthesis
Background:
- Gregatins are a class of natural products with potential biological activities.
- Efficient synthetic routes are crucial for further biological evaluation and analog development.
Purpose of the Study:
- To report the first total synthesis of (+)-gregatin E.
- To develop a new synthetic route for (+)-gregatin B.
- To establish the absolute configuration of (+)-gregatin E.
Main Methods:
- Palladium-catalyzed cyclization-methoxycarbonylation of optically active propargylic acetate.
- Suzuki-Miyaura coupling reaction.
- Copper thiophene-2-carboxylate (CuTC)-mediated coupling reaction.
Main Results:
- Successful total synthesis of (+)-gregatin E.
- Development of a novel synthetic pathway for (+)-gregatin B.
- Proposed absolute configuration of (+)-gregatin E as (5R,5'S).
Conclusions:
- The developed synthetic strategies are effective for constructing complex gregatins.
- The proposed absolute configuration provides valuable stereochemical information.
- This work enables further studies on gregalin analogs.
