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Updated: Jun 29, 2026
09:50
Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade
Published on: August 14, 2019
Synthesis of FF8181-A.
Noriaki Kobayashi1, Hidenobu Kuniyoshi, Ken Ishigami
1Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Tokyo, Japan.
Bioscience, Biotechnology, and Biochemistry
|October 8, 2008
Summary
Both enantiomers of FF8181-A were synthesized using a 15-step optical resolution method. The study determined the natural product
Area of Science:
- Organic Chemistry
- Stereochemistry
- Natural Product Synthesis
Background:
- Natural products are a source of novel therapeutics.
- Stereochemistry is crucial for biological activity.
- FF8181-A is a natural product with potential pharmacological relevance.
Purpose of the Study:
- To synthesize both enantiomers of FF8181-A.
- To determine the absolute configuration of FF8181-A.
- To establish a synthetic route for FF8181-A.
Main Methods:
- Diels-Alder reaction for initial product formation.
- Optical resolution for enantiomer separation.
- Multi-step synthesis (15 steps) for FF8181-A.
Main Results:
- Successful synthesis of both enantiomers of FF8181-A.
- Determination of the absolute configuration as 1S,5S,5aS,9aS,9bS.
- Established a 15-step synthetic pathway.
Conclusions:
- The synthesis of FF8181-A enantiomers was achieved.
- The absolute configuration of the natural product was confirmed.
- The developed synthetic route provides access to FF8181-A for further studies.
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