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

Autor:	Felix S. Pashkovsky, Fedor A. Lakhvich, Igor P. Lokot
Rok vydání:	1999
Předmět:	Stereochemistry Streptomyces viridochromogenes Organic Chemistry Thermal transformation Ionic bonding Germicidin Biochemistry Acylation chemistry.chemical_compound chemistry 2-Pyrone Drug Discovery Organic chemistry lipids (amino acids peptides and proteins)
Zdroj:	Tetrahedron. 55:4783-4792
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(99)00150-7
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::578f25a5a0cb888e476fadd021fa22ac https://doi.org/10.1016/s0040-4020(99)00150-7 Zobrazit plný text záznamu Full Text from ScienceDirect