Acyloxylation of Cyclic Enones: Synthesis of Densely Oxygenated Guaianolides | Zendy

Rubén MarínBarrios | Zendy; Ana Leticia GarcíaCabeza | Zendy; F. Javier MorenoDorado | Zendy; Francisco M. Guerra | Zendy; Guillermo M. Massanet | Zendy

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Acyloxylation of Cyclic Enones: Synthesis of Densely Oxygenated Guaianolides

Author(s) -

Rubén MarínBarrios,

Ana Leticia GarcíaCabeza,

F. Javier MorenoDorado,

Francisco M. Guerra,

Guillermo M. Massanet

Publication year - 2014

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo500915r

Subject(s) - carboxylic acid , chemistry , reaction conditions , substrate (aquarium) , scope (computer science) , organic chemistry , compatibility (geochemistry) , catalysis , materials science , computer science , composite material , oceanography , geology , programming language

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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