7 シガトキシンの全合成研究(口頭発表の部)  [in Japanese] 7 SYNTHETIC STUDIES OF CIGUATOXIN  [in Japanese]

    • 大石 徹 Oishi Tohru
    • 東北大院理:CREST Department of Chemistry, Graduate School of Science, Tohoku University:CREST, Japan Science and Technology Corporation
    • 大栗 博毅 Oguri Hiroki
    • 東北大院理:CREST Department of Chemistry, Graduate School of Science, Tohoku University:CREST, Japan Science and Technology Corporation
    • 前田 賢二 Maeda Kenji
    • 東北大院理:CREST Department of Chemistry, Graduate School of Science, Tohoku University:CREST, Japan Science and Technology Corporation
    • 南雲 陽子 Nagumo Yoko
    • 東北大院理:CREST Department of Chemistry, Graduate School of Science, Tohoku University:CREST, Japan Science and Technology Corporation

    • 庄司 満 Shoji Mitsuru
    • 東北大院理:CREST Department of Chemistry, Graduate School of Science, Tohoku University:CREST, Japan Science and Technology Corporation
    • Le Brazidec J.-Y.
    • 東北大院理:CREST Department of Chemistry, Graduate School of Science, Tohoku University:CREST, Japan Science and Technology Corporation
    • 丸山 潤美 Maruyama Megumi
    • 東北大院理:CREST Department of Chemistry, Graduate School of Science, Tohoku University:CREST, Japan Science and Technology Corporation

    • 佐々木 信也 Sasaki Shin-ya
    • 東北大院理:CREST Department of Chemistry, Graduate School of Science, Tohoku University:CREST, Japan Science and Technology Corporation
    • 今井 浩人 Imai Hiroto
    • 東北大院理:CREST Department of Chemistry, Graduate School of Science, Tohoku University:CREST, Japan Science and Technology Corporation
    • 上原 久俊 Uehara Hisatoshi
    • 東北大院理:CREST Department of Chemistry, Graduate School of Science, Tohoku University:CREST, Japan Science and Technology Corporation
    • 平間 正博 Hirama Masahiro
    • 東北大院理:CREST Department of Chemistry, Graduate School of Science, Tohoku University:CREST, Japan Science and Technology Corporation

Abstract

Ciguatera is a widespread human scale food poisoning that is caused by fishes dwelling in coral reefs in the tropics and subtropics. Ciguatoxis (CTX1B, 1 and CTX3C, 2), regarded as the principal toxins of ciguatera, were isolated from the moray eel, Gymnothorax javanicus, and the absolute configuration of 1 was determined as shown in Figure 1. Synthesis of ciguatoxins has recieved considarable attention among synthetic chemists due to the striking feature and biological features of these toxins. We developed a new method useful for constructing polycyclic ether systems based on alkylation and ring-closing metathesis reaction, and successfully synthesized the ABCDE ring moieties of ciguatoxin using this technique strating with the iodide 4 and ester 5 corresponding to the AB and E ring, respectively. Alternatively, we synthesized the IJKLM ring fragment via successive esterification of the alcohol 23 and carboxylic acid 24, Tebbe olefination, and ring-closing metathesis sequences, and the chemo- and stereoselective reduction of the methyl acetal. Studies toward total synthesis of ciguatoxin are currently underway.

Journal

天然有機化合物討論会講演要旨集   [List of Volumes]

天然有機化合物討論会講演要旨集 (41), 37-42, 1999-09-01  [Table of Contents]

Symposium on the chemistry of natural products

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Codes

  • NII Article ID (NAID) :
    110006681802
  • NII NACSIS-CAT ID (NCID) :
    AN00154136
  • Text Lang :
    JPN
  • Databases :
    NII-ELS 

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