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. Epub 2024 Jan 10.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents* / chemistry
  • Fungi*
  • Mycotoxins / chemistry
  • Structure-Activity Relationship

Substances

  • Anti-Infective Agents
  • sambutoxin
  • Mycotoxins