31 改良合成法を基盤とした(+)-デカルバモイルサキシトキシンおよび(+)-ゴニオトキシン3の全合成(口頭発表の部)

• 岩本 理

  東農工大院工

• 篠原 涼子

  東農工大院工

• 此木 敬一

  東北大院農

• 山下 まり

  東北大院農

• 長澤 和夫

  東農工大院工

書誌事項

タイトル別名

• Total Synthesis of (+)-Decarbamoylsaxitoxin and (+)-Gonyautoxin 3 on Developed Synthetic Method

抄録

Saxitoxin (STX) (2) and its analogues known as causative agents of paralytic shellfish poisoning, so called PSP, are potent neurotoxins produced by harmful dinoflagellates. This fatal intoxication is attributed to STXs' potent affinity against the voltage gated sodium channels (NaChs), thus the toxins strongly block the influx of sodium ion and inhibit the depolarization process of neuronal cells. We have recently accomplished total synthesis of (-) and (+)-doSTX (ent-2 and 2) and (+)-STX (1) by the use of 1,3-dipolar cycloaddition reaction and unique IBX oxidation reaction. In this paper, we described the NaCh inhibitory activity of novel synthetic STX derivatives 19-22. We also succeeded in developing the new synthetic methodology for constructing the cyclic guanidine skeleton under the extremely mild conditions, which successfully allow us to the total synthesis of (+)-dcSTX (3) and (+)-GTX3 (7) from "protected" saxitoxinol 34.

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 51 (0), 181-186, 2009

  天然有機化合物討論会実行委員会

詳細情報

• CRID: 1390282681054986496
• NII論文ID: 110009757638
• DOI: 10.24496/tennenyuki.51.0_181
• 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