Laboratório de Semioquímicos, Departamento de Química, Universidade Federal do Paraná, UFPR, Caixa Postal 19020, Curitiba 81531-990, PR, Brazil.
Departamento de Química, Universidade Federal de Santa Maria, Avda. Roraima, 1000, Santa Maria, RS, Brazil.
Nat Prod Rep. 2023 Apr 26;40(4):866-889. doi: 10.1039/d2np00068g.
Covering: 2013 to June 2022Pheromones are usually produced by insects in sub-microgram amounts, which prevents the elucidation of their structures by nuclear magnetic resonance (NMR). Instead, a synthetic reference material is needed to confirm the structure of the natural compounds. In addition, the provision of synthetic pheromones enables large-scale field trials for the development of environmentally friendly pest management tools. Because of these potential applications in pest control, insect pheromones are attractive targets for the development of synthetic procedures and the synthesis of these intraspecific chemical messengers has been at the core of numerous research efforts in the field of pheromone chemistry. The present review is a quick reference guide for the syntheses of insect pheromones published from 2013 to mid-2022, listing the synthesized compounds and highlighting current methodologies in organic synthesis, such as carbon-carbon coupling reactions, organo-transition metal chemistry including ring-closing olefin metathesis, asymmetric epoxidations and dihydroxylations, and enzymatic reactions.
2013 年至 2022 年 6 月 信息素通常由昆虫以亚微克量产生，这使得通过核磁共振（NMR）来阐明其结构变得困难。相反，需要合成参考材料来确认天然化合物的结构。此外，提供合成信息素可以为开发环保型害虫管理工具进行大规模田间试验。由于这些在害虫防治方面的潜在应用，昆虫信息素成为合成程序开发的有吸引力的目标，并且这些种内化学信使的合成一直是信息素化学领域众多研究努力的核心。本综述是 2013 年至 2022 年年中发表的昆虫信息素合成的快速参考指南，列出了合成的化合物，并强调了有机合成中的当前方法，例如碳-碳偶联反应、包括闭环烯烃复分解在内的有机过渡金属化学、不对称环氧化和双羟化反应以及酶反应。
