Related Experiment Video
Updated: Jun 5, 2026

Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities
Published on: October 2, 2018
Synthesis of the C'D'E'F' domain of maitotoxin
K C Nicolaou1, Jae Hong Seo, Tsuyoshi Nakamura
1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States. kcn@scripps.edu
Abstract:
A devised biomimetic strategy toward the C'D'E'F' domain (6) of maitotoxin (1) led to hydroxy triepoxide 8 as a postulated polyepoxide precursor. However, all attempts to induce the desired cascade to form the targeted compound through a zip-type reaction under neutral or acidic conditions failed, prompting adoption of a linear stepwise approach to 6. The successful synthetic strategy for the synthesis of the C'D'E'F' domain of maitotoxin commenced from furfuryl alcohol (11), proceeded through F' ring building block 15, and involved two regio- and stereoselective intramolecular hydroxy epoxide openings and a stereoselective SmI(2)-mediated ring closure to forge rings C', E', and D', respectively. (13)C NMR spectroscopic analysis of the synthesized domain (6) and comparisons with previous results confirmed the original structural assignment of this region of maitotoxin. X-ray crystallographic analysis of 6 provided unambiguous proof of its structure.
Related Concept Videos
Bacterial Toxins
Diphtheria
Botulism
ATP Synthase: Mechanism
Types of Toxins
Air pollutants, primarily gases, pose significant threats to respiratory health, leading to conditions like hypoxia, lung cancer, and in extreme cases, death.
Environmental pollutants like...
Master Transcription Regulators

