Issue 20, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis and antifouling activity of 3-isocyanotheonellin and its analogues

Yoshikazu Kitano,*a   Toshihiro Ito,a   Takehiro Suzuki,a   Yasuyuki Nogata,b   Kyouji Shinshima,b   Erina Yoshimura,c   Kazuhiro Chiba,a   Masahiro Tadaa  and  Isamu Sakaguchib  

* Corresponding authors

a Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan
E-mail: kitayo@cc.tuat.ac.jp
Fax: +81 42 360 8830
Tel: +81 42 367 5863

b Abiko Research Laboratory, Central Research Institute of Electric Power Industry, 1646 Abiko, Abiko, Chiba 270-1194, Japan

c Bio-environment Research Co. Ltd., 1-6-1 Ogawa-cho, Kanda, Tokyo 101-0052, Japan

Abstract

A new synthesis of 3-isocyanotheonellin, a marine sesquiterpene with potent antifouling activity against the larvae of the barnacle Balanus amphirite, and its analogues is described. The highlight of the synthetic strategy is the one-step construction of a tertiary isocyanide from an alcohol using trimethylsilyl cyanide and a silver salt. The antifouling activities of 3-isocyanotheonellin and its analogues are also reported.

Graphical abstract: Synthesis and antifouling activity of 3-isocyanotheonellin and its analogues

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Article information

DOI
https://doi.org/10.1039/B206705F
Article type
Paper
Submitted
11 Jul 2002
Accepted
20 Aug 2002
First published
23 Sep 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 2251-2255

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Synthesis and antifouling activity of 3-isocyanotheonellin and its analogues

Y. Kitano, T. Ito, T. Suzuki, Y. Nogata, K. Shinshima, E. Yoshimura, K. Chiba, M. Tada and I. Sakaguchi, J. Chem. Soc., Perkin Trans. 1, 2002, 2251 DOI: 10.1039/B206705F

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