Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Diversifying Complexity by Domino Benzannulation of Polycyclic Natural Products

Diversifying Complexity by Domino Benzannulation of Polycyclic Natural Products
Gonzalo J. Mena-Rejón, Rosina Dapueto, Rubén M. Carballo, Fernando García-Tellado, Samuel Delgado-Hernández, David Tejedor
Herein we describe a salicylaldehyde-annulation reaction as a plug and play toolkit to diversify the complexity of naturally occurring ketones. The protocol entails the transformation of the polycyclic natural ketone into its propargyl vinyl ether derivative (two synthetic steps) and its microwave-assisted imidazole-catalyzed domino rearrangement to generate the salicylaldehyde ring. This annexed unit allows further synthetic transformations: e.g., the installation of a pharmacophore module to generate natural product–pharmacophore hybrids endowed with unknown biological (pharmaceutical) annotations.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00654

DOI: 10.1021/acs.joc.7b00654

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