Total synthesis of (−)-domoic acid, a potent ionotropic glutamate receptor agonist and the key compound in oceanic harmful algal blooms-Reference-Cited by-同舟云学术

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

Published:2023 Issue:8 Volume:21 Page:1653-1656
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Nishizawa Shigeru¹,Ouchi Hitoshi¹^ORCID,Suzuki Hiroto¹,Ohnishi Takuma¹,Sasaki Shingo¹,Oyagi Yu¹,Kanakogi Masaki¹,Matsumura Yoshitaka¹,Nakagawa Shunsuke¹,Asakawa Tomohiro¹,Egi Masahiro¹,Inai Makoto¹^ORCID,Yoshimura Fumihiko¹^ORCID,Takita Ryo¹^ORCID,Kan Toshiyuki¹

Affiliation:

1. School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan

Abstract

The stereo-controlled total synthesis of (−)-domoic acid is described, including the crucial formation of the trisubstitutedZ-olefin moiety and the incorporation of the side chain using modified Julia–Kocieński reaction in the final stage.

Funder

Japan Agency for Medical Research and Development

Ministry of Education, Culture, Sports, Science and Technology

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2023/OB/D2OB02325C

Reference45 articles.

1. Ligands for Glutamate Receptors: Design and Therapeutic Prospects

2. Domoic acid induced spinal cord lesions in adult mice: Evidence for the possible molecular pathways of excitatory amino acids in spinal cord lesions

3. Acromelic acid is a much more potent excitant than kainic acid or domoic acid in the isolated rat spinal cord

4. Constituents of Chondria armata

5. Studies on the Constituents of Chondria armata. I