Tetrahedron

A rapid and diverse construction of 6-substituted-5, 6-dihydro-4-hydroxy-2-pyrones through double Reformatsky reaction

M Mineno, Y Sawai, K Kanno, N Sawada, H Mizufune

Index: Mineno, Masahiro; Sawai, Yasuhiro; Kanno, Kazuaki; Sawada, Naotaka; Mizufune, Hideya Tetrahedron, 2013 , vol. 69, # 51 p. 10921 - 10926

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Abstract

Abstract A rapid and diverse synthesis of biologically important 6-substituted-5, 6-dihydro-4- hydroxy-2-pyrones through a double Reformatsky reaction of aldehydes to δ-hydroxy-β- ketoesters followed by lactonization is described. Due to the high functional group tolerance and reaction site discrimination between aldehyde, nitrile, and ester groups in the substrate, the protocol can provide the dihydropyrones with bromo, nitro, carboxylic acid, and β- ...