Total synthesis of ciguatoxin and 51-hydroxyCTX3C |
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Authors: | Inoue Masayuki Miyazaki Keisuke Ishihara Yuuki Tatami Atsushi Ohnuma Yuyu Kawada Yuuya Komano Kazuo Yamashita Shuji Lee Nayoung Hirama Masahiro |
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Institution: | Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan. inoue@ykbsc.chem.tohoku.ac.jp |
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Abstract: | Ciguatoxins, the principal causative toxins of ciguatera seafood poisoning, are large ladder-like polycyclic ethers with the 13 ether rings ranging from five- to nine-membered. In this paper, we describe the total synthesis of the two most toxic members of the ciguatoxin family, ciguatoxin 1 and 51-hydroxyCTX3C 2, based on a unified synthetic strategy. The key features in our syntheses were (i) direct construction of the O,S-acetal from the corresponding left and right wing fragments (3, 4, 14); (ii) stereo- and chemoselective radical reaction of the alpha-oxyradical with pentafluorophenyl acrylate to achieve cyclization of the seven-membered G-ring; (iii) ring-closing metathesis reaction to build the nine-membered F-ring; and (iv) an efficient protective group strategy using the oxidatively removable 2-naphthylmethyl groups. |
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