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Total Synthesis of Cinnamodial-Based Dimer (-)-Capsicodendrin
1Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Republic of Korea.
The Journal of Organic Chemistry
|May 7, 2020
Summary
Researchers achieved the first total synthesis of (-)-capsicodendrin, a dimer derived from (-)-cinnamodial. This discovery reveals (-)-capsicodendrin as a potential insecticidal chemical reservoir in plants.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Chemical Ecology
Background:
- The Cinnamosma genus produces sesquiterpenoids with potential insecticidal properties.
- (-)-Cinnamodial is a key sesquiterpenoid found in these plants.
- The dimeric form, (-)-capsicodendrin, has not been previously synthesized.
Purpose of the Study:
- To achieve the first total synthesis of (-)-capsicodendrin.
- To investigate the relationship between (-)-cinnamodial and (-)-capsicodendrin.
- To explore the potential ecological role of (-)-capsicodendrin in plant defense.
Main Methods:
- Development of a 12-step synthetic route to (-)-cinnamodial from 1-vinyl-2,6,6-trimethylcyclohexene.
- Kinetically controlled base-catalyzed dimerization of (-)-cinnamodial to (-)-capsicodendrin.
- Investigation of the facile conversion of (-)-capsicodendrin back to (-)-cinnamodial.
Main Results:
- Successful synthesis of (-)-cinnamodial.
- Selective dimerization of (-)-cinnamodial to (-)-capsicodendrin under specific conditions.
- Demonstration of the reversible conversion between (-)-capsicodendrin and (-)-cinnamodial.
Conclusions:
- (-)-Capsicodendrin can be synthesized from (-)-cinnamodial.
- (-)-Capsicodendrin may serve as a chemical reservoir for insecticidal (-)-cinnamodial.
- Plants of the Cinnamosma genus might release (-)-cinnamodial from (-)-capsicodendrin in response to environmental stress.
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