Jietacins with potent nematocidal activity; Efficient isolation of novel analogs and divergent total synthesis of jietacin A, B, C, and D the paper is dedicated to Professor Iwao Ojima on the occasion of his 70th birthday

Akihiro Sugawara, Masahiko Kubo, Takuji Nakashima, Tomoyasu Hirose, Noriaki Tsunoda, Kyoichi Yahagi, Yukihiro Asami, Takeshi Yamada, Kazuro Shiomi, Yoko Takahashi, Satoshi Omura, Toshiaki Sunazuka

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2149-2157
Number of pages9
JournalTetrahedron
Volume71
Issue number14
DOIs
Publication statusPublished - 2015 Apr 8
Externally publishedYes

Keywords

  • Grignard reaction
  • Isolation
  • Structure elucidation
  • Total synthesis
  • Vinyl azoxy

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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