Title:	Microwave-assisted enantioselective synthesis of (2R,5S)-theaspirane: a green chemistry approach.
Authors:	SI, S. C. S. T. da MORAES, M. C. B. BORGES, M. LAUMANN, R. A. MARAVALHO, I. V. SILVA, W. A.
Affiliation:	SAYURI 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.
Date Issued:	2025
Citation:	Molecules, v. 30, n. 7, 1519, 2025.
Description:	The 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
NAL Thesaurus:	Semiochemicals Green chemistry
Keywords:	Microwave-assisted reactions (2R 5S)-theaspirane Kinetic resolution Cyclization Stereoselective synthesis
DOI:	https://doi.org/10.3390/molecules30071519
Notes:	Na publicação: Sayuri Cristina Santos Takada; Maria Carolina Blassioli-Moraes.
Type of Material:	Artigo de periódico
Access:	openAccess
Appears in Collections:	Artigo em periódico indexado (CENARGEN)