Related Experiment Videos
Isostrychnine synthesis mediated by hypervalent iodine reagent
Guillaume Jacquemot1, Gaëtan Maertens, Sylvain Canesi
1Département de chimie, Université du Québec à Montréal, Laboratoire de Méthodologie et Synthèse de Produits Naturels, C.P. 8888, Succ. Centre-Ville, Montréal, H3C 3P8, Québec (Canada), Fax: (+1) 514-987-4054.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 3, 2015
Summary
Researchers developed a novel synthetic route to strychnine, a recognized alkaloid, using a key oxidative dearomatizing process. This new method efficiently synthesizes strychnine and isostrychnine from a common phenol precursor.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Medicinal Chemistry
Background:
- Strychnine is a complex and widely recognized alkaloid with significant biological activity.
- Existing synthetic routes to strychnine are often lengthy and complex.
- Development of novel and efficient synthetic strategies is crucial for accessing complex natural products.
Purpose of the Study:
- To report an unexplored synthetic route to strychnine and isostrychnine.
- To utilize a hypervalent iodine-mediated oxidative dearomatizing process as a key synthetic step.
- To achieve efficient synthesis from a readily available phenol precursor.
Main Methods:
- Employing a hypervalent iodine-mediated oxidative dearomatizing process.
- Utilizing an aza Michael-ether-enol tandem transformation.
- Incorporating two Heck-type cyclizations, reductive isomerization, and cascade double reductive amination.
Main Results:
- Successful synthesis of isostrychnine in nine steps and strychnine in ten steps.
- Demonstration of a novel and efficient synthetic pathway.
- Access to the core alkaloid structure through a cascade of reactions.
Conclusions:
- The reported synthetic route offers a new and efficient method for accessing strychnine and isostrychnine.
- The key oxidative dearomatizing step provides a powerful tool for complex alkaloid synthesis.
- This approach highlights the potential of hypervalent iodine chemistry in natural product synthesis.