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Updated: Jul 18, 2026
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A High-throughput-compatible FRET-based Platform for Identification and Characterization of Botulinum Neurotoxin Light Chain Modulators
Published on: December 27, 2013
A concise total synthesis of DL-histrionicotoxin
Maheswaran S Karatholuvhu1, Alex Sinclair, Annabella F Newton
1School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich NR4 7TJ, United Kingdom.
Journal of the American Chemical Society
|September 28, 2006
Summary
A novel nine-step synthesis of (+/-)-histrionicotoxin was developed using a two-directional strategy. This efficient approach enables rapid access to this complex natural product.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Natural Product Synthesis
Background:
- Histrionicotoxin is a complex natural product with significant biological activity.
- Efficient synthetic routes are crucial for studying and utilizing such compounds.
Purpose of the Study:
- To develop a concise and efficient synthesis of (+/-)-histrionicotoxin.
- To explore the utility of a two-directional synthesis strategy for complex molecule construction.
Main Methods:
- Two-directional synthesis strategy.
- Key reactions: two-directional cross-metathesis, tandem cascade reactions (oxime formation/Michael addition/1,4-prototopic shift/[3 + 2]-cycloaddition), selective Z,Z-bisenyne formation, and one-pot reductions.
Main Results:
- Achieved synthesis of (+/-)-histrionicotoxin in nine steps.
- Demonstrated the effectiveness of the two-directional approach and key cascade reactions.
Conclusions:
- The developed nine-step synthesis provides an efficient route to (+/-)-histrionicotoxin.
- The synthetic strategy highlights advancements in complex molecule synthesis through cascade reactions and two-directional approaches.
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