Synthesis of new, potent avermectin-like insecticidal agents.
4'-Modified avermectin derivatives were designed and synthesized. Some of the new synthetic compounds showed excellent in vivo bioactivity against cabbage larvae when compared to commercially available avermectin B1a. In this synthesis, uncommon thioglycosyl sugar donors, prepared from the hydrolysis of natural antibiotics, proved compatible with sugar-macrolide synthesis in the presence of N-iodosuccinimide (NIS) or I2 in N-methylpyrrolidone at room temperature.
Wei
Lijun
L
School of Chemistry and Material Engineering, Yunnan University, Kunming City, Kunming 650091, China.
Wei
Guohua
G
Zhang
Houcheng
H
Wang
Peng G
PG
Du
Yuguo
Y
D000818:Animals; D007306:Insecticides / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D007455:Iodine / Q000737:chemistry; D007559:Ivermectin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D007814:Larva / Q000187:drug effects; D051379:Mice; D011759:Pyrrolidines / Q000737:chemistry; D013388:Succinimides / Q000737:chemistry
D007306:Insecticides; D011759:Pyrrolidines; D013388:Succinimides; C054965:N-methylpyrrolidine; C008155:N-iodosuccinimide; C022120:avermectin B(1)a; D007559:Ivermectin; D007455:Iodine