Tetrahedron p. 4783 - 4792 (1999)
Update date:2022-08-11
Topics:
Lokot, Igor P.
Pashkovsky, Felix S.
Lakhvich, Fedor A.
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 approach has been demonstrated in the synthesis of rac-germicidin, an autoregulative germination inhibitor of Streptomyces viridochromogenes NRRL B-1551.
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