Takada Sayuri Cristina Santos, Blassioli-Moraes Maria Carolina, Borges Miguel, Laumann Raul Alberto, Maravalho Izabella Vitória, Silva Wender Alves
Embrapa Genetic Resources and Biotechnology, Empresa Brasileira de Pesquisa Agropecuaria, Brasilia 70770-917, Brazil.
Laboratory for Bioactive Compound Synthesis, University of Brasilia (IQ-UnB), Campus Universitario Darcy Ribeiro, Brasilia 70904-970, Brazil.
Molecules. 2025 Mar 29;30(7):1519. doi: 10.3390/molecules30071519.
The banana weevil () is a significant pest that reduces banana yields and can result in plant mortality. (2,5)-theaspirane, a kairomone from senesced banana leaves, is one of the natural banana volatiles, aiding weevil attraction. A rapid and cost-effective synthesis of (2,5)-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.
香蕉象甲是一种严重的害虫，会降低香蕉产量并可能导致植株死亡。（2,5）-茶螺烷是一种来自衰老香蕉叶的信息素，是天然香蕉挥发物之一，有助于吸引象甲。利用微波辅助条件和绿色化学原理，开发了一种快速且经济高效的（2,5）-茶螺烷合成方法。该过程包括五个步骤，从二氢-β-紫罗兰酮的还原开始，接着是脂肪酶介导的动力学拆分以获得高对映体过量。微波辅助加热显著缩短了反应时间。采用了用最少二氧化硒氧化量的优化环化反应。通过色谱法分离最终的非对映异构体，得到对映体纯度超过99%的化合物。
