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Total synthesis of (-)-domoic acid, a potent ionotropic glutamate receptor agonist and the key compound in oceanic harmful algal blooms.

Shigeru NishizawaHitoshi OuchiHiroto SuzukiTakuma OhnishiShingo SasakiYu OyagiMasaki KanakogiYoshitaka MatsumuraShunsuke NakagawaTomohiro AsakawaMasahiro EgiMakoto InaiFumihiko YoshimuraRyo TakitaToshiyuki Kan
Published in: Organic & biomolecular chemistry (2023)
The stereo-controlled total synthesis of (-)-domoic acid is described. The critical construction of the C1'-C2' Z -configuration was accomplished by taking advantage of an unsaturated lactam structure. The side chain fragment was introduced in the final stages of synthesis through a modified Julia-Kocieński reaction, aiming for its efficient derivatization.
Keyphrases
  • ms ms
  • high performance liquid chromatography
  • liquid chromatography
  • simultaneous determination
  • mass spectrometry
  • gas chromatography
  • high resolution mass spectrometry