Abstract
Jietacin compounds are known to display potent nematocidal activity being 10-fold more active against the pine wood nematode (Bursaphelenchus lignicolus) than avermectin B1a. They consist of a unique functional vinylazoxy group. Herein, we disclose not only the isolation of novel analogs (jietacin C and D) but also a divergent and a 7-step total synthesis for jietacin A, B, C, and (S and R) D in 30–36% overall yield, incorporating reductive hydrazination, regioselective azoxy formation, and C–C bond formation via acylation using Grignard reagents in the presence of vinylazoxy moiety at the final stage. In addition, we evaluated the nematocidal activity of jietacin A–D and synthetic intermediates against Caenorhabditis elegans as a model nematode.
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