Jietacins with potent nematocidal activity; efficient isolation of novel analogs and divergent total synthesis of jietacin A, B, C, and D
A Sugawara, M Kubo, T Nakashima, T Hirose… - Tetrahedron, 2015 - Elsevier
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 …
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 …
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