Acyloxylation of Cyclic Enones: Synthesis of Densely Oxygenated Guaianolides

作者:Marin Barrios Ruben; Leticia Garcia Cabeza Ana; Javier Moreno Dorado F; Guerra Francisco M; Massanet Guillermo M
来源:Journal of Organic Chemistry, 2014, 79(14): 6501-6509.
DOI:10.1021/jo500915r

摘要

The alpha%26apos;-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.

  • 出版日期2014-7-18