A versatile method for the synthesis of γ-pyrones

…, A Karagiannis, A Kazemeini…

Index: Beye, Garrison E.; Karagiannis, Athanasios; Kazemeini, Alieh; Ward, Dale E. Canadian Journal of Chemistry, 2012 , vol. 90, # 11 p. 954 - 964

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Abstract

A versatile three-step procedure to annulate a γ-pyrone onto a methylene ketone was developed involving (i) aldol reaction with a dithiolane-protected β-ketoaldehyde,(ii) oxidation of the aldol adduct to a β-diketone, and (iii) treatment of the resulting dithiolane- protected 1, 3, 5-trione with 2-iodoxybenzoic acid (IBX) and trifluoromethanesulfonic acid (triflic acid; TfOH) in acetonitrile at ambient temperature to give the corresponding γ- ...