title: Acyloxylation of cyclic enones: synthesis of densely oxygenated guaianolides.
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.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz , 11510 Puerto Real, Cádiz, Spain.
authors.forename: Rubén
authors.initials: R
authors.lastname: Marín-Barrios
authors.forename: Ana Leticia
authors.initials: AL
authors.lastname: García-Cabeza
authors.forename: F Javier
authors.initials: FJ
authors.lastname: Moreno-Dorado
authors.forename: Francisco M
authors.initials: FM
authors.lastname: Guerra
authors.forename: Guillermo M
authors.initials: GM
authors.lastname: Massanet