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

Abstract

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
29 Dec 2022
Accepted
24 Jan 2023
First published
25 Jan 2023

Org. Biomol. Chem., 2023, Advance Article

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

S. Nishizawa, H. Ouchi, H. Suzuki, T. Ohnishi, S. Sasaki, Y. Oyagi, M. Kanakogi, Y. Matsumura, S. Nakagawa, T. Asakawa, M. Egi, M. Inai, F. Yoshimura, R. Takita and T. Kan, Org. Biomol. Chem., 2023, Advance Article , DOI: 10.1039/D2OB02325C

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