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Diversifying Complexity by Domino Benzannulation of Polycyclic Natural Products

AuthorsTejedor, David ; Delgado-Hernández, Samuel; Carballo, Ruben M.; Dapueto, Rosina; Mena-Rejón, Gonzalo J.; García-Tellado, Fernando
Issue Date3-May-2017
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 82(10): 5328-5336 (2017)
AbstractHerein 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 version (URL)http://dx.doi.org/10.1021/acs.joc.7b00654
Appears in Collections:(IPNA) Artículos
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