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Total Synthesis of (+)-Arborisidine
Zhiyao Zhou1, Alison X Gao1, Scott A Snyder1
1Department of Chemistry , University of Chicago , 5735 South Ellis Avenue , Chicago , Illinois 60637 , United States.
Journal of the American Chemical Society
|April 25, 2019
Summary
Researchers achieved the first total synthesis of arborisidine, a complex Kopsia indole alkaloid. This involved novel methods for creating challenging quaternary carbon centers, offering a new route to this unique natural product.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Medicinal Chemistry
Background:
- Arborisidine is a unique Kopsia indole alkaloid.
- Its structure features a fully substituted cyclohexanone ring with two quaternary carbons.
- Synthesizing such complex structures presents significant challenges in stereocontrol.
Purpose of the Study:
- To achieve the first total synthesis of arborisidine.
- To develop efficient and stereoselective methods for constructing its complex core.
- To explore new synthetic strategies for indole alkaloids.
Main Methods:
- A seven-step racemic synthesis from tryptamine.
- A nine-step asymmetric synthesis from d-tryptophan methyl ester.
- Key steps included a decyanation protocol for aza-quaternary center formation and a metal-promoted enyne cyclization.
Main Results:
- Successful total synthesis of arborisidine in both racemic and asymmetric forms.
- Efficient construction of the two challenging quaternary carbon centers.
- Demonstrated regiospecific functionalizations of a complex diene intermediate.
Conclusions:
- The developed synthetic route is distinct and efficient.
- The strategy overcomes challenges in accessing optically active aza-quaternary centers.
- This work provides a valuable foundation for further studies on Kopsia alkaloids.
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