2. Academic Validation
  3. Total Synthesis of Fusaramin, Enabling Stereochemical Elucidation, Structure-Activity Relationship, and Uncovering the Hidden Antimicrobial Activity against Plant Pathogenic Fungi

Total Synthesis of Fusaramin, Enabling Stereochemical Elucidation, Structure-Activity Relationship, and Uncovering the Hidden Antimicrobial Activity against Plant Pathogenic Fungi

  • Org Lett. 2024 Jan 26;26(3):597-601. doi: 10.1021/acs.orglett.3c03792.
Aoi Kimishima 1 2,  Daichi Hagimoto 1,  Masako Honsho 1 2,  Katsuyuki Sakai 1,  Sota Honma 1 2,  Shin-Ichi Fuji 3,  Masato Iwatsuki 1 2,  Toshiyuki Tokiwa 2,  Kenichi Nonaka 4,  Takumi Chinen 5,  Takeo Usui 6,  Yukihiro Asami 1 2
Affiliations

Affiliations

  • 1 Graduate School of Infection Control Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
  • 2 O̅mura Satoshi Memorial Institute, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
  • 3 Faculty of Bioresource Sciences, Akita Prefectural University, 241-438 Nakanokaidoubatanishi, Shimoshinjo, Akita, Akita 010-0195, Japan.
  • 4 Faculty of Life and Environmental Sciences, Teikyo University of Science, 2-2-1 Senjusakuragi, Adachi-ku, Tokyo 120-0045, Japan.
  • 5 Graduate School of Life and Environmental Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8572, Japan.
  • 6 Institute of Life and Environmental Science, Teikyo University of Science, 2-2-1 Senjusakuragi, Adachi-ku, Tokyo 120-0045, Japan.
PMID: 38198624 DOI: 10.1021/acs.orglett.3c03792
Abstract

Fusaramin (1) was isolated as a mitochondrial inhibitor. However, the Fungal producer stops producing 1, which necessitates us to supply 1 by total synthesis. We proposed the complete stereochemical structure based on the biosynthetic pathway of sambutoxin. We have established concise and robust total synthesis of 1, enabling us to determine the complete stereochemical structure and to elucidate the structure-activity relationship, and uncover the hidden antiplant pathogenic Fungal activity.

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