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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MDPI AG
2025-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/7/1519 |
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| author | Sayuri Cristina Santos Takada Maria Carolina Blassioli-Moraes Miguel Borges Raul Alberto Laumann Izabella Vitória Maravalho Wender Alves Silva |
| author_facet | Sayuri Cristina Santos Takada Maria Carolina Blassioli-Moraes Miguel Borges Raul Alberto Laumann Izabella Vitória Maravalho Wender Alves Silva |
| author_sort | Sayuri Cristina Santos Takada |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-753ff5d6ef4e4e57a714e177d20bddc7 |
| institution | OA Journals |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-753ff5d6ef4e4e57a714e177d20bddc72025-08-20T02:09:14ZengMDPI AGMolecules1420-30492025-03-01307151910.3390/molecules30071519Microwave-Assisted Enantioselective Synthesis of (2<i>R</i>,5<i>S</i>)-Theaspirane: A Green Chemistry ApproachSayuri Cristina Santos Takada0Maria Carolina Blassioli-Moraes1Miguel Borges2Raul Alberto Laumann3Izabella Vitória Maravalho4Wender Alves Silva5Embrapa Genetic Resources and Biotechnology, Empresa Brasileira de Pesquisa Agropecuaria, Brasilia 70770-917, BrazilEmbrapa Genetic Resources and Biotechnology, Empresa Brasileira de Pesquisa Agropecuaria, Brasilia 70770-917, BrazilEmbrapa Genetic Resources and Biotechnology, Empresa Brasileira de Pesquisa Agropecuaria, Brasilia 70770-917, BrazilEmbrapa Genetic Resources and Biotechnology, Empresa Brasileira de Pesquisa Agropecuaria, Brasilia 70770-917, BrazilLaboratory for Bioactive Compound Synthesis, University of Brasilia (IQ-UnB), Campus Universitario Darcy Ribeiro, Brasilia 70904-970, BrazilLaboratory for Bioactive Compound Synthesis, University of Brasilia (IQ-UnB), Campus Universitario Darcy Ribeiro, Brasilia 70904-970, BrazilThe 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.https://www.mdpi.com/1420-3049/30/7/1519microwave-assisted reactions(2<i>R</i>,5<i>S</i>)-theaspiranesemiochemicalskinetic resolutiongreen chemistrycyclization |
| spellingShingle | Sayuri Cristina Santos Takada Maria Carolina Blassioli-Moraes Miguel Borges Raul Alberto Laumann Izabella Vitória Maravalho Wender Alves Silva Microwave-Assisted Enantioselective Synthesis of (2<i>R</i>,5<i>S</i>)-Theaspirane: A Green Chemistry Approach Molecules microwave-assisted reactions (2<i>R</i>,5<i>S</i>)-theaspirane semiochemicals kinetic resolution green chemistry cyclization |
| title | Microwave-Assisted Enantioselective Synthesis of (2<i>R</i>,5<i>S</i>)-Theaspirane: A Green Chemistry Approach |
| title_full | Microwave-Assisted Enantioselective Synthesis of (2<i>R</i>,5<i>S</i>)-Theaspirane: A Green Chemistry Approach |
| title_fullStr | Microwave-Assisted Enantioselective Synthesis of (2<i>R</i>,5<i>S</i>)-Theaspirane: A Green Chemistry Approach |
| title_full_unstemmed | Microwave-Assisted Enantioselective Synthesis of (2<i>R</i>,5<i>S</i>)-Theaspirane: A Green Chemistry Approach |
| title_short | Microwave-Assisted Enantioselective Synthesis of (2<i>R</i>,5<i>S</i>)-Theaspirane: A Green Chemistry Approach |
| title_sort | microwave assisted enantioselective synthesis of 2 i r i 5 i s i theaspirane a green chemistry approach |
| topic | microwave-assisted reactions (2<i>R</i>,5<i>S</i>)-theaspirane semiochemicals kinetic resolution green chemistry cyclization |
| url | https://www.mdpi.com/1420-3049/30/7/1519 |
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