155553-70-1Relevant articles and documents
Evaluation of heteroatom-rich derivatives as antitubercular agents with InhA inhibition properties
Moulkrere, Bachar Rébat,Orena, Beatrice S.,Mori, Giorgia,Saffon-Merceron, Nathalie,Rodriguez, Frédéric,Lherbet, Christian,Belkheiri, Nadji,Amari, Mohamed,Hoffmann, Pascal,Fodili, Mokhtar
, p. 308 - 320 (2018/04/19)
Two series of heterocyclic compounds derived from 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one (DHA) and 2-acetylbutyrolactone have been synthesized and characterized. The compounds were evaluated for their activities against Mycobacterium tuberculosis stra
A new approach to the synthesis of 3,6- and 5,6-dialkyl derivatives of 4-hydroxy-2-pyrone. Synthesis of rac-germicidin
Lokot, Igor P.,Pashkovsky, Felix S.,Lakhvich, Fedor A.
, p. 4783 - 4792 (2007/10/03)
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.
Structures and Stereochemistries of New Compounds Related to Alternaric Acid
Tabuchi, Hiroyasu,Ichihara, Akitami
, p. 125 - 134 (2007/10/02)
Three alternaric acid-related compounds, viz., 10-deoxyalternaric acid 2, 10-deoxy-6,19-dihydroalternaric acid 3, and 10-deoxy-6,8,9,19-tetrahydroalternaric acid 4, have been isolated from Alternaria solani which is a causal fungus of early blight disease
Total synthesis and stereochemistry of alternaric acid
Tabuchi,Hamamoto,Miki,Tejima,Ichihara
, p. 4749 - 4759 (2007/10/02)
Determination of the stereochemistry and the total synthesis of alternaric acid 1 has been achieved. The stereostructure of 1 has been elucidated by stereoselective synthesis of four diastereoisomers of the C(9)-C(14) fragment 6, which had been obtained as a degradation product during structural studies. Key reactions of the total synthesis of 1 include the Julia olefination of tertiary aldehyde 6 and phenylsulfone 7 and novel one-pot construction of 3-acyl-4-hydroxy-5,6-dihydro-2-pyrone via Fries-type rearrangement of the O-enol acyl group of β-keto-δ-valerolactone toward the α-position of the δ-lactone. The absolute configuration of alternaric acid has been shown to be that illustrated in structure 1. The modified Fries-type rearrangement method has also been extended to the synthesis of some other compounds containing a tricarbonylmethane structure.
Metabolites of Lachnellula fuscosanguinea (Rehm). Part 1. The isolation, structure determination, and synthesis of lachnelluloic acid
Ayer, William A.,Villar, J. Daniel Figueroa
, p. 1161 - 1165 (2007/10/02)
The metabolites produced in liquid culture by the fungus Lachnellula fuscosanguinea (Rehm) Dennis have been examined and two antifungal agents, lachnelluloic acid and lachnellulone, have been isolated.The structure of lachnelluloic acid has been established as (-)-4-hydroxy-3-octanoyl-6-pentyl-5,6-dihydro-2-pyrone (1) by chemical and spectroscopic methods.The total synthesis of racemic lachnelluloic acid, starting from 6,8-tridecanedione (6) is reported.Lachnelluloic acid (1) shows strong antifungal activity against Ceratocystis ulmi, the causative agent of Dutch elm disease.
Structure et syntheses nouvelles dans la serie des amino-4-dihydro-5,6- methyl-6 pyrones-2
Nedjar-Kolli, Bellara,Hamdi, Maamar,Perie, Jacques,Herault, Valentin
, p. 543 - 547 (2007/10/02)
Primary and secondary amines react with 4-hydroxy-5,6-dihydro-2-pyrones at position 4, and not at position 2 as previously indicated.However, a new series of compounds is obtained by this reaction, some of them exhibiting therapeutic properties.Reactiviti
