Dihydropyrans from Pyruvates in a One-Pot Reaction (No. 0022)

 
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Summary

Dihydropyran is an essential structure often found in a variety of pharmaceuticals, in multiple compounds used for drug discovery, and in other bioactive products. The common practice used today to generate dihydropyran derivatives is through non-enzymatic reactions of pyruvates. However, these methods suffer from multiple setbacks including the difficulty to control the dual reactivities of pyruvates reactions, they require high temperatures, and do not provide the ability to form subsequent dihydropyran derivatives in one-pot reactions. A novel catalytic method developed by a group of researchers led by Prof. Fujie Tanaka, enables generation of functionalized dihydropyran derivatives in concise reactions from pyruvates with aldehydes, to form a wide range of functionalized molecules. This set of reactions is performed under mild conditions and as a one-pot process to produce pure products.

 

Lead Researcher:
Fujie Tanaka

Faculty of Chemistry and Chemical Bioengineering Unit

Applications

  • Drug Discovery
  • Therapeutic Medicine

 

Advantages

  • A simple, one-pot process
  • Mild conditions (products can be obtained at 25 degC
  • High yield
  • A single diastereomer under optimized conditions
  • A wide variety of dihydropyran derivatives

Figure 1. (a) One-pot reaction of pyruvates, which generates functionalized dihydropyran derivatives 1. (b) Various functionalized molecules synthesized from dihydropyran 1 in consecutive reactions.

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Technology's Essence

The researchers showed that with the use of appropriate catalysts and conditions, the dual reactivities of pyruvates could be managed to generate functionalized dihydropyran derivatives (dihydropyran 1) in non-enzymatic reactions. These can be further synthesized in a one-pot cascade reaction to generate various functionalized molecules synthesized from dihydropyran 1. For this purpose, several catalysts were tested, with the catalyst pyrrolidine-3-carboxylic acid (b-proline) showing the best results. The optimized reaction was performed using ethyl pyruvate, aldehyde, and b-proline, in CH3CN at 25 degC. In this process, the dihydropyran product was obtained in 72% yield, primarily as a single diastereomer.

 

Media Coverage and Presentations

 

CONTACT FOR MORE INFORMATION

  Graham Garner
Technology Licensing Section

  tls@oist.jp
  +81(0)98-966-8937