12 シガトキシンの絶対構造決定への合成化学的アプローチ(口頭発表の部)

• 佐藤 大

  東北大・理

• 鈴木 敏夫

  東北大・理

• 平間 正博

  東北大・理

• 村田 道雄

  東北大・農

• 安元 健

  東北大・農

• 原田 宣之

  東北大・反応化学研

書誌事項

タイトル別名

• 12 Enantioselective Synthesis of the AB Ring Fragment of Gambiertoxin 4B. Implication for the Absolute Configuration of Gambiertoxin 4B and Ciguatoxin

抄録

Twenty thousand of people in subtropical and tropical regions have suffered annually from ciguatera caused by poisonous fishes dwelling in coral reefs. In 1989 Yasumoto et al. established the whole structures including relative stereochemistry of the causative principle, ciguatoxin (CTX, 1), isolated from moray eel, Gymnothorax javanicus, and its congener, gambiertoxin 4B (GT4B, 2), from epiphytic dinoflagellate, Gambierdiscus toxicus (Fig. 1). Extremely low accessibility of these toxins, however, hampers further studies on their absolute configuration, pharmacological studies at the molecular level and development of immunoassay for differentiating poisonous fishes. Therefore, determination of the absolute stereochemistry and the chemical syntheses are critical and of great interest. The AB ring framework of gambiertoxin 4B (3) which has a butadienyl substituent on the tetrahydrooxepin ring A has been synthesized stereoselectively (Scheme 2) and its CD spectrum (Fig. 2) suggests that gambiertoxin 4B (2) and ciguatoxin (1) have 5R configuration.

収録刊行物

• 天然有機化合物討論会講演要旨集

  天然有機化合物討論会講演要旨集 33 (0), 86-93, 1991

  天然有機化合物討論会実行委員会

詳細情報

• CRID: 1390001206079913472
• NII論文ID: 110006678980
• DOI: 10.24496/tennenyuki.33.0_86
• ISSN: 24331856
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可