Open AccessNew Insecticidal Agents from Halogenation/Acylation of the Furyl-Ring of Fraxinellone
Author(s) -
Yong Guo,
Ruige Yang,
Hui Xu
Publication year - 2016
Publication title -
scientific reports
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.24
H-Index - 213
ISSN - 2045-2322
DOI - 10.1038/srep35321
Subject(s) - halogenation , ring (chemistry) , steric effects , chemistry , halogen , acylation , reagent , stereochemistry , medicinal chemistry , organic chemistry , catalysis , alkyl
of the halogen atom or the acyl group at the C-ring of fraxinellone was investigated. Some unexpected halogenation products were obtained with the different chlorination/bromination reagents, and their possible reaction mechanisms were also proposed. Seven key steric structures of 2a’, 2b, 2b’, 2c’, 3a, 3b, and one isomer (5’α-Cl) of 2a were further confirmed by single-crystal X-ray diffraction. Especially compounds 2a, 2a’, 3a and 3c exhibited more potent insecticidal activity than toosendanin. Some structure-activity relationships of tested compounds were also described.