Microwave-Assisted Enantioselective Synthesis of (2<i>R</i>,5<i>S</i>)-Theaspirane: A Green Chemistry Approach
The banana weevil (<i>Cosmopolites sordidus</i>) is a significant pest that reduces banana yields and can result in plant mortality. (2<i>R</i>,5<i>S</i>)-theaspirane, a kairomone from senesced banana leaves, is one of the natural banana volatiles, aiding weevil a...
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| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-03-01
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| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/30/7/1519 |
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| Summary: | The banana weevil (<i>Cosmopolites sordidus</i>) is a significant pest that reduces banana yields and can result in plant mortality. (2<i>R</i>,5<i>S</i>)-theaspirane, a kairomone from senesced banana leaves, is one of the natural banana volatiles, aiding weevil attraction. A rapid and cost-effective synthesis of (2<i>R</i>,5<i>S</i>)-theaspirane was developed utilizing microwave-assisted conditions and the principles of green chemistry. The process comprised five steps, beginning with the reduction of dihydro-β-ionone, followed by lipase-mediated kinetic resolution to attain high enantiomeric excess. Microwave-assisted heating significantly reduced reaction times. Optimized cyclization with the minimum quantities of selenium dioxide oxidation was employed. The final diastereomers were separated by chromatography, yielding compounds which exceeded 99% enantiomeric purity. |
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| ISSN: | 1420-3049 |