Tetrahedron

A new approach to the synthesis of 3, 6-and 5, 6-dialkyl derivatives of 4-hydroxy-2-pyrone. Synthesis of rac-germicidin

IP Lokot, FS Pashkovsky, FA Lakhvich

Index: Lokot, Igor P.; Pashkovsky, Felix S.; Lakhvich, Fedor A. Tetrahedron, 1999 , vol. 55, # 15 p. 4783 - 4792

Full Text: HTML

Citation Number: 42

Abstract

A new approach to the synthesis of 3, 6-and 5, 6-dialkyl-4-hydroxy-2-pyrones has been developed. The method includes the formation of acylated Meldrum's acids (5-(2-alkyl-3- oxoacyl)-2, 2-dimethyl-1, 3-dioxane-4, 6-diones) followed by their thermal transformation. Introduction of 3-alkyl substituents was accomplished by acylation of 4-hydroxy-2-pyrones and ionic hydrogenation of the 3-acyl derivatives obtained. The effectiveness of this new ...