ortho-Quinol Acetate Chemistry: Reactivity toward Aryl-Based Nucleophiles and Applications to the Synthesis of Natural Products.

J Org Chem

Institut des Sciences Moléculaires, Univ. Bordeaux, ISM (CNRS-UMR 5255) , 351 cours de la Libération, 33405 Talence, France.

Published: April 2017

Two model ortho-quinol acetates were easily prepared by iodane-mediated acetoxylative phenol dearomatization and evaluated for their reactivity toward various aryl-based nucleophiles, i.e., aryl metallic reagents and phenolic derivatives. Novel modes of reactivity, allowing the formation of biaryl linkages, were revealed and here exploited for the synthesis of two natural phenolics.

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http://dx.doi.org/10.1021/acs.joc.7b00250DOI Listing

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Two model ortho-quinol acetates were easily prepared by iodane-mediated acetoxylative phenol dearomatization and evaluated for their reactivity toward various aryl-based nucleophiles, i.e., aryl metallic reagents and phenolic derivatives.

View Article and Find Full Text PDF

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