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. 1998 Dec 15;8(24):3643-6.
doi: 10.1016/s0960-894x(98)00674-x.

Synthesis of gem-difluoro-avermectin derivatives: potent anthelmintic and anticonvulsant agents

P T Meinke  1 , W L Shoop, B F Michael, T A Blizzard, G R Dawson, M H Fisher, H Mrozik
Affiliations

Synthesis of gem-difluoro-avermectin derivatives: potent anthelmintic and anticonvulsant agents

P T Meinke et al. Bioorg Med Chem Lett. .

Abstract

A series of gem-difluoro-avermectin derivatives was synthesized from the corresponding ketones at positions 4", 4', 13, and 23 using diethylaminosulfur trifluoride (DAST). These fluorinated avermectins exhibit potent antiparasitic activity in a new Haemonchus contortus larval assay and are equipotent to ivermectin. In addition, 23-gem-difluoro-ivermectin displays useful anticonvulsant activity in mouse models.

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