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Synthesis of kaempferitrin.

Sameer Urgaonkar¹, Jared T Shaw

¹Chemical Biology Program, Broad Institute of Harvard and MIT, 7 Cambridge Center, Cambridge, Massachusetts 02142, USA.

The Journal of Organic Chemistry

|May 15, 2007

Summary

Researchers report a concise synthesis of Kaempferitrin, a natural compound. This work enables the creation of new Kaempferitrin derivatives for studying its biological activity.

Area of Science:

Organic Chemistry
Natural Product Synthesis
Glycosylation Chemistry

Background:

Kaempferitrin is a 3,7-diglycosylflavone with potential biological activity.
Efficient synthesis of complex natural products is crucial for further research.

Purpose of the Study:

To develop a short and efficient synthetic route for Kaempferitrin.
To enable the preparation of Kaempferitrin derivatives for biological studies.

Main Methods:

Synthesis of a differentially protected kaempferol intermediate.
First reported bis-glycosylation of a dihydroxyflavone.

Main Results:

Successful short synthesis of Kaempferitrin (1).
Demonstration of selective protection of kaempferol's hydroxyl groups.

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Achieved the first bis-glycosylation of a dihydroxyflavone.

Conclusions:

The developed synthetic strategy provides access to Kaempferitrin and its derivatives.
This work facilitates future investigations into the biological origins and activities of Kaempferitrin.