Microwave-assisted enantioselective synthesis of (2R,5S)-theaspirane: a green chemistry approach.

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dc.contributorSAYURI CRISTINA SANTOS TAKADA DA SI, CENARGEN; MARIA CAROLINA BLASSIOLI MORAES, CENARGEN; MIGUEL BORGES, CENARGEN; RAUL ALBERTO LAUMANN, CENARGEN; IZABELLA VITÓRIA MARAVALHO, UNIVERSITY OF BRASILIA; WENDER ALVES SILVA, UNIVERSITY OF BRASILIA.
dc.creatorSI, S. C. S. T. da
dc.creatorMORAES, M. C. B.
dc.creatorBORGES, M.
dc.creatorLAUMANN, R. A.
dc.creatorMARAVALHO, I. V.
dc.creatorSILVA, W. A.
dc.date2025-05-27T17:48:04Z
dc.date2025-05-27T17:48:04Z
dc.date2025-05-27
dc.date2025
dc.date.accessioned2026-07-07T11:56:17Z
dc.descriptionThe banana weevil (Cosmopolites sordidus) is a significant pest that reduces banana yields and can result in plant mortality. (2R,5S)-theaspirane, a kairomone from senesced banana leaves, is one of the natural banana volatiles, aiding weevil attraction. A rapid and cost-effective synthesis of (2R,5S)-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
dc.descriptionNa publicação: Sayuri Cristina Santos Takada; Maria Carolina Blassioli-Moraes.
dc.identifierMolecules, v. 30, n. 7, 1519, 2025.
dc.identifierhttp://www.alice.cnptia.embrapa.br/alice/handle/doc/1176055
dc.identifierhttps://doi.org/10.3390/molecules30071519
dc.identifier.urihttp://hdl.handle.net/123456789/518217
dc.languageeng
dc.rightsopenAccess
dc.subjectMicrowave-assisted reactions
dc.subject(2R 5S)-theaspirane
dc.subjectKinetic resolution
dc.subjectCyclization
dc.subjectStereoselective synthesis
dc.subjectSemiochemicals
dc.subjectGreen chemistry
dc.titleMicrowave-assisted enantioselective synthesis of (2R,5S)-theaspirane: a green chemistry approach.
dc.typeArtigo de periódico

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