Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (2): 519-525.DOI: 10.6023/cjoc202109018 Previous Articles     Next Articles


Palmarumycin B6类似物的合成及杀蚊活性

刘鑫磊, 许磊川, 安鑫鲲, 蒋家珍, 王明安*()   

  1. 中国农业大学应用化学系 农药创新研究中心 北京 100193
  • 收稿日期:2021-09-13 修回日期:2021-09-29 发布日期:2022-02-24
  • 通讯作者: 王明安
  • 基金资助:

Synthesis and Larvicidal Activity of Palmarumycin B6 Analogues

Xinlei Liu, Leichuan Xu, Xinkun An, Jiazhen Jiang, Ming'an Wang()   

  1. Innovation Center of Pesticide Research, Department of Applied Chemistry, China Agricultural University, Beijing 100193
  • Received:2021-09-13 Revised:2021-09-29 Published:2022-02-24
  • Contact: Ming'an Wang
  • Supported by:
    National Natural Science Foundation of China(21772229)

In order to improve the biological activity of naturally occurring Palmarumycin B6, the synthesis of Palmarumycin B6 chlorine- and fluorine-containing analogues at A ring has been achieved via ketalization of substituted 1-tetralone enol ether with 1,8-dihydroxynaphthalene and the benzyl oxidation involving pyridinium dichromate and t-BuOOH as the key steps. Their structures were fully characterized by 1H NMR, 13C NMR, and HR-ESI-MS data. Their larvicidal activities were evaluated and showed that 6-chloro-5-hydroxy-2,3-dihydro-4H-spiro[naphthalene-1,2'-naphtho[1,8-de]-[1,3]dioxin]-4-one (4m) and 6-fluoro-5-hydroxy-2,3-dihydro-4H-spiro[naphthalene-1,2'-naphtho[1,8-de][1,3]dioxin]-4-one (4i) were the most active compounds with the LC50 values of 11.51 and 23.25 µg/mL against Aedes albopictus, and they would be the potential lead structure to be optimized. The halogen atoms at C-6, 5-hydroxy and 4-carbonyl play a critical role for the larvicidal activities of this type of Palmarumycin B6 analogues.

Key words: spirobisnaphthalene, Palmarumycin B6, ketalization, benzyl oxidation, larvicidal activity