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Total Synthesis of Chrysosporazines B and C
Xiaoyu Fang1, Yu Jiang1, Yuhan Xiao1
1School of Pharmacy and Food Engineering, Wuyi University, Jiangmen, Guangdong 529020, China.
Organic Letters
|February 2, 2026
Summary
Researchers achieved the first total synthesis of chrysosporazines B and C. This complex synthesis utilized stereoselective methods, including Suzuki-Miyaura coupling and asymmetric hydrogenation, to build the target molecules.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Medicinal Chemistry
Background:
- Chrysosporazines B and C are complex natural products with potential biological activity.
- Previous synthetic routes for these compounds were lacking, hindering further research.
Purpose of the Study:
- To achieve the first total synthesis of chrysosporazines B and C.
- To develop a concise and stereoselective synthetic strategy.
Main Methods:
- Suzuki-Miyaura coupling of an E-enol tosylate.
- Rhodium-catalyzed asymmetric hydrogenation for constructing the diaryl amino acid motif.
- Piperazinedione condensation and reduction for piperazine ring formation.
- Palladium-catalyzed carbonylation for scaffold assembly.
Main Results:
- Successful and stereoselective total synthesis of chrysosporazines B and C.
- Overall yields of 9.2% for chrysosporazine B and 8.0% for chrysosporazine C.
- Efficient construction of the hexahydro-6H-pyrazino[1,2-b]isoquinolin-6-one core structure.
Conclusions:
- The developed synthetic route is efficient and highly stereoselective.
- This synthesis provides access to chrysosporazines B and C for further biological evaluation.
- The methodology can be applicable to the synthesis of related natural products.
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