Related Experiment Video
Updated: Oct 13, 2025
11:04
Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
3.1K
Total Synthesis and Structural Assignment of (-)-Fusaequisin A
Ann-Christin Schmidt1, Martin Hiersemann1
1Fakultät für Chemie und Chemische Biologie, TU Dortmund, 44227, Dortmund, Germany.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 11, 2021
Summary
Researchers synthesized (-)-Fusaequisin A, a fungal polyketide, clarifying its structure. This work provides a synthetic route and corrects the initial structural assignment of this natural product.
Area of Science:
- Natural Product Synthesis
- Organic Chemistry
- Mycology
Background:
- (-)-Fusaequisin A is a polyketide from Fusarium equiseti with an undetermined absolute configuration.
- It shares a backbone with curvicollide C, highlighting structural similarities in fungal metabolites.
Purpose of the Study:
- To achieve the total synthesis of (-)-Fusaequisin A and its 4-O-desmethyl derivative.
- To establish the constitution and absolute configuration of (-)-Fusaequisin A.
Main Methods:
- Utilized a central-to-lateral building block strategy for synthesis.
- Employed key C/C-connecting transformations: catalytic asymmetric Claisen rearrangement, Julia-Kocienski olefination, and olefin cross-metathesis.
Main Results:
- Successfully synthesized (-)-Fusaequisin A and its 4-O-desmethyl derivative.
- Deduced the constitution and absolute configuration, leading to a revised structural assignment.
- Established a reliable synthetic pathway for this class of polyketides.
Conclusions:
- The total synthesis confirmed the structure of (-)-Fusaequisin A.
- The study corrected the initial structural assignment, providing definitive stereochemical information.
- This research contributes to the understanding of fungal polyketide biosynthesis and chemistry.
