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Oxidative 1,2- and 1,3-alkyl shift processes: developments and applications in synthesis.

Kimiaka C Guérard¹, Amandine Guérinot, Cloé Bouchard-Aubin

¹Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, H3C 3P8 Quebec, Canada.

The Journal of Organic Chemistry

|February 16, 2012

Summary

This study introduces a novel oxidative alkyl shift reaction using hypervalent iodine to efficiently modify aromatic compounds. The method rapidly creates complex molecular scaffolds found in bioactive natural products.

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Area of Science:

Organic Chemistry
Synthetic Chemistry
Medicinal Chemistry

Background:

Phenol derivatives are common starting materials in organic synthesis.
Developing efficient methods for constructing complex molecular scaffolds is crucial for drug discovery.
Hypervalent iodine reagents offer unique reactivity for oxidative transformations.

Purpose of the Study:

To develop a novel oxidative alkyl shift reaction for phenol derivatives.
To generate highly functionalized scaffolds with potential applications in natural product synthesis.
To establish an enantioselective version for creating challenging quaternary carbon centers.

Main Methods:

Oxidative 1,2- and 1,3- alkyl shifts mediated by a hypervalent iodine reagent.
Application to simple and inexpensive phenol derivatives.
Development of an enantioselective variant of the reaction.

Main Results:

Rapid redesign of aromatic skeletons yielding functionalized scaffolds.
Formation of prochiral dienone systems and quaternary carbon centers.
Successful enantioselective synthesis of a challenging quaternary carbon center.

Conclusions:

The described method provides efficient access to complex molecular cores of bioactive natural products.
The reaction enables rapid synthesis of functionalized polycyclic systems.
Demonstrated potential through formal synthesis of acetylaspidoalbidine, a natural product alkaloid.