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

doi:10.1016/j.tet.2015.02.038

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

11 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 language	English
Pages (from-to)	2149-2157
Number of pages	9
Journal	Tetrahedron
Volume	71
Issue number	14
DOIs	https://doi.org/10.1016/j.tet.2015.02.038
Publication status	Published - 2015 Apr 8
Externally published	Yes

Keywords

Grignard reaction
Isolation
Structure elucidation
Total synthesis
Vinyl azoxy

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Sugawara, A., Kubo, M., Nakashima, T., Hirose, T., Tsunoda, N., Yahagi, K., Asami, Y., Yamada, T., Shiomi, K., Takahashi, Y., Omura, S., & Sunazuka, T. (2015). 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. Tetrahedron, 71(14), 2149-2157. https://doi.org/10.1016/j.tet.2015.02.038

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. / Sugawara, Akihiro; Kubo, Masahiko; Nakashima, Takuji et al.

In: Tetrahedron, Vol. 71, No. 14, 08.04.2015, p. 2149-2157.

Research output: Contribution to journal › Article › peer-review

Sugawara, A, Kubo, M, Nakashima, T, Hirose, T, Tsunoda, N, Yahagi, K, Asami, Y, Yamada, T, Shiomi, K, Takahashi, Y, Omura, S & Sunazuka, T 2015, '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', Tetrahedron, vol. 71, no. 14, pp. 2149-2157. https://doi.org/10.1016/j.tet.2015.02.038

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title = "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",

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.",

keywords = "Grignard reaction, Isolation, Structure elucidation, Total synthesis, Vinyl azoxy",

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

note = "Funding Information: We thank a Grant for the 21st Century COE Program , a Grant-in-Aid for Scientific Research on Innovative Areas {\textquoteleft}Chemical Biology of Natural Products{\textquoteright} ( 24102527 , 26102737 to AS), together with funds from the Quality Assurance Framework of Higher Education from The Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan. We also thank Professor Shohei Mitani (Tokyo Women's Medical University) for kind gift of C. elegans and Dr. Kenichiro Nagai and Ms. Noriko Sato (Kitasato University) for various instrumental analyses. Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd. All rights reserved.",

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doi = "10.1016/j.tet.2015.02.038",

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AU - Sugawara, Akihiro

AU - Kubo, Masahiko

AU - Nakashima, Takuji

AU - Hirose, Tomoyasu

AU - Tsunoda, Noriaki

AU - Yahagi, Kyoichi

AU - Asami, Yukihiro

AU - Yamada, Takeshi

AU - Shiomi, Kazuro

AU - Takahashi, Yoko

AU - Omura, Satoshi

AU - Sunazuka, Toshiaki

N1 - Funding Information: We thank a Grant for the 21st Century COE Program , a Grant-in-Aid for Scientific Research on Innovative Areas ‘Chemical Biology of Natural Products’ ( 24102527 , 26102737 to AS), together with funds from the Quality Assurance Framework of Higher Education from The Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan. We also thank Professor Shohei Mitani (Tokyo Women's Medical University) for kind gift of C. elegans and Dr. Kenichiro Nagai and Ms. Noriko Sato (Kitasato University) for various instrumental analyses. Publisher Copyright: © 2015 Elsevier Ltd. All rights reserved.

PY - 2015/4/8

Y1 - 2015/4/8

N2 - 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.

AB - 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.

KW - Grignard reaction

KW - Isolation

KW - Structure elucidation

KW - Total synthesis

KW - Vinyl azoxy

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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

Abstract

Keywords

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