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Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade
Published on: August 14, 2019
Total synthesis of ochnaflavone
Monica M Ndoile1, Fanie R van Heerden
1School of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X01, Scottsville 3209, Pietermaritzburg, South Africa.
Beilstein Journal of Organic Chemistry
|August 16, 2013
Summary
Researchers achieved the first total synthesis of ochnaflavone, an asymmetric biflavone. Key steps involved diaryl ether formation and chalcone cyclization to construct the flavone nuclei.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Medicinal Chemistry
Background:
- Ochnaflavone is an asymmetric biflavonoid with potential biological activities.
- Previous synthetic routes for complex biflavonoids have been limited.
- The structural complexity of ochnaflavone presents a significant synthetic challenge.
Purpose of the Study:
- To achieve the first total synthesis of ochnaflavone.
- To synthesize the permethyl ether of 2,3,2'',3''-tetrahydroochnaflavone.
- To establish optimal conditions for key synthetic transformations.
Main Methods:
- Formation of a diaryl ether linkage between apigenin and luteolin precursors.
- Ring cyclization of an ether-linked dimeric chalcone intermediate.
- Optimization of oxidative cyclization conditions for biflavone assembly.
Main Results:
- Successful total synthesis of ochnaflavone.
- Successful synthesis of the permethyl ether of 2,3,2'',3''-tetrahydroochnaflavone.
- Identification of optimal conditions for the oxidative cyclization step.
Conclusions:
- The study reports the first successful total syntheses of ochnaflavone and a related derivative.
- The developed synthetic strategy provides a viable route to access complex asymmetric biflavonoids.
- This work lays the foundation for further exploration of biflavonoid chemistry and biological evaluation.
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