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From a Natural Product to Its Biosynthetic Gene Cluster: A Demonstration Using Polyketomycin from Streptomyces diastatochromogenes Tü6028

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Total Synthesis of Kopsone.

Kazutoshi Tomoya¹, Kazuaki Komiya¹, Daisuke Nakajima¹

¹Graduate School of Pharmaceutical Sciences, Nagoya University, Nagoya 464-8601, Japan.

Organic Letters

|April 10, 2023

Summary

This study details the total synthesis of kopsone, a complex molecule. Key steps included a stereoselective Ireland-Claisen rearrangement and a nitrone cycloaddition to construct the bicyclic core.

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Area of Science:

Organic Chemistry
Synthetic Chemistry
Medicinal Chemistry

Background:

Kopsone is a complex natural product with potential biological activity.
Efficient synthetic routes are crucial for further study and analog development.

Purpose of the Study:

To achieve the first total synthesis of kopsone.
To develop a stereoselective and efficient synthetic strategy.

Main Methods:

Ireland-Claisen rearrangement for stereoselective aldehyde synthesis.
Intramolecular cycloaddition of an eight-membered cyclic nitrone.
Construction of the 2-azabicyclo[3.3.1]nonane core.

Main Results:

Successful total synthesis of kopsone.
Stereoselective preparation of a key acyclic aldehyde intermediate.
Formation of the target 2-azabicyclo[3.3.1]nonane skeleton.

Conclusions:

The developed synthetic route is effective for kopsone preparation.
The strategy provides a foundation for synthesizing kopsone analogs.
This synthesis advances the field of complex molecule synthesis.