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Acyloxylation of Cyclic Enones: Synthesis of Densely Oxygenated Guaianolides

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URI: http://hdl.handle.net/10498/20367

DOI: 10.1021/jo500915r

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2014-Acyloxylation of cyclic enones. Synthesis of densely oxygenated guaianolides.pdf (1.004Mb)
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Author/s
Marín Barrios, Rubén; García-Cabeza, Ana Leticia; Moreno Dorado, Francisco JavierAuthority UCA; Guerra, Francisco M.; Martínez Massanet, Guillermo
Date
2014-06
Department
Química Orgánica
Source
Journal of Organic Chemistry 2014, 79, 6501−6509
Abstract
The α′-acyloxylation of cyclic enones with linear carboxylic acids is described. The reaction is promoted by KMnO4 in the presence of a carboxylic acid and its corresponding carboxylic anhydride. The optimization of the reaction has been carried out using the statistical methodology known as design of experiments. The optimized reaction conditions have been evaluated in terms of substrate scope and compatibility with different functional groups. The methodology has been applied to the synthesis of densely oxygenated guaianes and guaianolides.
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Attribution-NonCommercial-NoDerivatives 4.0 Internacional
This work is under a Creative Commons License Attribution-NonCommercial-NoDerivatives 4.0 Internacional

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