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Updated: Mar 2, 2026
11:44
Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities
Published on: October 2, 2018
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First total synthesis of concavine.
François Saint-Dizier1, Nigel S Simpkins1
1School of Chemistry , University of Birmingham , Edgbaston , Birmingham , B15 2TT , UK .
Chemical Science
|May 17, 2017
Summary
Researchers synthesized the alkaloid concavine from Clitocybe concava. This study clarifies the natural product
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Mycology
Background:
- Concavine is an unusual alkaloid isolated from the mushroom Clitocybe concava.
- The structure and properties of natural concavine require further elucidation.
Purpose of the Study:
- To achieve the total synthesis of concavine.
- To clarify the structural identity of the natural product.
Main Methods:
- Regio- and stereoselective synthesis of polycyclic imide intermediates.
- Enolate substitution and Grignard addition reactions.
- A novel sulfenylative radical cyclisation for bridge formation.
Main Results:
- Successful synthesis of concavine.
- NMR data indicated the original natural product data likely represented an acetic acid salt artifact.
- The synthetic route provides a reliable method for accessing concavine.
Conclusions:
- The total synthesis of concavine was accomplished.
- The reported NMR data for natural concavine was likely due to an artifact.
- This work provides a validated synthetic pathway for concavine and clarifies its structure.
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