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Updated: Jun 11, 2026

Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade

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Published on: August 14, 2019

Total synthesis of syringolin A.

Chunhui Dai¹, Corey R J Stephenson

¹Department of Chemistry, Boston University, Boston, Massachusetts 02215, USA.

Organic Letters

|July 6, 2010

Summary

Researchers synthesized syringolin A efficiently in 13 steps. This method provides access to analogues of this promising proteasome inhibitor, aiding drug discovery.

Area of Science:

Organic Chemistry
Medicinal Chemistry
Chemical Synthesis

Background:

Syringolin A is a promising proteasome inhibitor.
Developing efficient synthetic routes is crucial for drug development.

Purpose of the Study:

To achieve a convergent and efficient synthesis of syringolin A.
To establish a method for creating analogues of syringolin A.

Main Methods:

The synthesis utilized Garner's aldehyde and L-valine as starting materials.
Key reactions included Johnson-Claisen and Curtius rearrangements for fragment preparation.
Macrolactamization and late-stage side chain introduction were employed.

Main Results:

A 13-step synthesis of syringolin A was successfully developed.

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The synthesis is efficient and starts from commercially available materials.

The route allows for the preparation of the unnatural 3,4-dehydrolysine fragment.

Conclusions:

The developed synthetic strategy is efficient and convergent.
This synthesis provides convenient access to analogues of syringolin A.
The findings facilitate further research into proteasome inhibitors.