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Furan-Site Bromination and Transformations of Fraxinellone as Insecticidal Agents Against Mythimna separata Walker

Furan ring of limoninoids is critical in exhibiting insecticidal activity. Herein, fraxinellone (1) was used as a template of furan-containing natural products and a series of its derivatives was synthesized by selective bromination in good yields on gram-scale and following Suzuki-Miyaura or Sonoga...

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Detalles Bibliográficos
Autores principales: Dong, Qing-Miao, Dong, Shuai, Shen, Cheng, Cao, Qing-Hao, Song, Ming-Yu, He, Qiu-Rui, Wang, Xiao-Ling, Yang, Xiao-Jun, Tang, Jiang-Jiang, Gao, Jin-Ming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5976728/
https://www.ncbi.nlm.nih.gov/pubmed/29849138
http://dx.doi.org/10.1038/s41598-018-26747-0
Descripción
Sumario:Furan ring of limoninoids is critical in exhibiting insecticidal activity. Herein, fraxinellone (1) was used as a template of furan-containing natural products and a series of its derivatives was synthesized by selective bromination in good yields on gram-scale and following Suzuki-Miyaura or Sonogashira coupling reactions in moderate to good yields. Bromination of limonin (9) was also accomplished without altering other functional groups in high yield. Furthermore, an evaluation of insecticidal activity against the instar larvae of Mythimna separata showed that derivatives 2, 3b, 3g, 5a, 5d and 5h displayed more potent insecticidal activity than 1 and toosendanin.