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Critical Importance of the Nine‐Membered F Ring of Ciguatoxin for Potent Bioactivity: Total Synthesis and Biological Evaluation of F‐Ring‐Modified Analogues

2008; Wiley; Volume: 47; Issue: 45 Linguagem: Inglês

10.1002/anie.200803921

1521-3773

Masayuki Inoue, Nayoung Lee, Keisuke Miyazaki, Toyonobu Usuki, Shigeru Matsuoka, Masahiro Hirama,

Synthetic Organic Chemistry Methods

Angewandte Chemie International EditionVolume 47, Issue 45 p. 8611-8614 Communication Critical Importance of the Nine-Membered F Ring of Ciguatoxin for Potent Bioactivity: Total Synthesis and Biological Evaluation of F-Ring-Modified Analogues† Masayuki Inoue Prof. Dr., Masayuki Inoue Prof. Dr. [email protected] Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-3395-5214Search for more papers by this authorNayoung Lee Dr., Nayoung Lee Dr. Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578 (Japan), Fax: (+81)-22-795-6566Search for more papers by this authorKeisuke Miyazaki Dr., Keisuke Miyazaki Dr. Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578 (Japan), Fax: (+81)-22-795-6566Search for more papers by this authorToyonobu Usuki Dr., Toyonobu Usuki Dr. Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578 (Japan), Fax: (+81)-22-795-6566Search for more papers by this authorShigeru Matsuoka Dr., Shigeru Matsuoka Dr. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-3395-5214Search for more papers by this authorMasahiro Hirama Prof. Dr., Masahiro Hirama Prof. Dr. [email protected] Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578 (Japan), Fax: (+81)-22-795-6566Search for more papers by this author Masayuki Inoue Prof. Dr., Masayuki Inoue Prof. Dr. [email protected] Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-3395-5214Search for more papers by this authorNayoung Lee Dr., Nayoung Lee Dr. Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578 (Japan), Fax: (+81)-22-795-6566Search for more papers by this authorKeisuke Miyazaki Dr., Keisuke Miyazaki Dr. Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578 (Japan), Fax: (+81)-22-795-6566Search for more papers by this authorToyonobu Usuki Dr., Toyonobu Usuki Dr. Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578 (Japan), Fax: (+81)-22-795-6566Search for more papers by this authorShigeru Matsuoka Dr., Shigeru Matsuoka Dr. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-3395-5214Search for more papers by this authorMasahiro Hirama Prof. Dr., Masahiro Hirama Prof. Dr. [email protected] Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578 (Japan), Fax: (+81)-22-795-6566Search for more papers by this author First published: 21 October 2008 https://doi.org/10.1002/anie.200803921Citations: 22 † This work was supported financially by SORST (Japan) Science and Technology Agency (JST) and a Grant-in-Aid for Scientific Research (S) from the Japan Society for the Promotion of Science (JSPS). A fellowship for K.M. and T.U. from the Japan Society for the Promotion of Science is gratefully acknowledged. We thank Prof. M. Satake (The University of Tokyo) for valuable suggestions. [3H]PbTx-3 was kindly provided by Prof. K. Tachibana (The University of Tokyo). Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Playing a central role: Ciguatoxins, potent neurotoxins, span a length of over 3 nm and consist of 13 fused ether rings (from the A to the M ring; see energy-minimized structure). The finding that two fully synthetic F-ring-modified analogues have markedly diminished biological activities demonstrates that the central F ring plays a major role in organizing the ciguatoxin molecule into a shape suitable for bioactivity. Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_200803921_sm_miscellaneous_information.pdf488.3 KB miscellaneous information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. 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