148159-54-0Relevant academic research and scientific papers
New formal syntheses of laurencione, a labile dihydrofuranone derivative from the red alga Laurencia spectabilis
De Kimpe, Norbert,Georgieva, Angelina,Boeykens, Marc,Kozekov, Ivan,Aelterman, Wim
, p. 1131 - 1134 (1996)
A straightforward formal synthesis of the marine natural product laurencione was developed, utilizing elaboration of 5-acetoxy-3-chloropentan-2-one as the starting compound. The synthetic route consisted of (i) α-sulfenylation, (ii) α-chlorination of the resulting β-oxo sulfide, (iii) Hg2+-catalyzed methanolysis, (iv) methanolysis of the γ-acetoxy-α,α-dimethoxy ketone with subsequent cyclization and (v) acid hydrolysis of the acetal. Alternatively, laurencione was prepared from 1,1-dichloroacetone by a sequence of reactions involving (i) imination, (ii) regiospecific β-hydroxyethylation, (iii) hydrolysis, (iv) base-induced rearrangement of the resulting functionalized tetrahydrofuran and (v) final acid hydrolysis of laurencione methyl ether.
Investigation of reactive α-dicarbonyl compounds generated from the maillard reactions of L -Methionine with reducing sugars via their stable quinoxaline derivatives
Pfeifer, Yvonne V.,Kroh, Lothar W.
experimental part, p. 8293 - 8299 (2011/04/24)
The formation of α-dicarbonyl compounds was investigated in methionine-catalyzed (Maillard reaction) thermal degradation of d-glucose, maltose, and dextrin 10 at three different pH values (3, 5, and 8). The α-dicarbonyl compounds were trapped as quinoxalines and could be quantified by HPLC and GC-MS. Formation of 1,4-dideoxypentodiulose from hexoses and disaccharides was evidenced for the first time. The use of L-methionine as the amino compound for the formation of 1,4-dideoxypentodiulose in model systems is explained. Furthermore, it could be shown that methionine has great effect on the formation of specific α-dicarbonyl compounds. At various pH values and also by application of mono-, di-, and oligosaccharides in all model reactions, 3-deoxyhexosulose and 1,4-dideoxypentodiulose were generated preferentially.
Synthesis of laurencione, a labile dihydro-3(2H)-furanone derivative from the red alga Laurencia spectabilis
De Kimpe,Georgieva,Boeykens,Lazar
, p. 5262 - 5265 (2007/10/02)
The first total synthesis of laurencione, a naturally occurring dihydro- 3(2H)-furanone derivative isolated from the red alga Laurencia spectabilis, is described. The synthesis is comprised (1) of conversion of γ- butyrolactone into α,α-dimethoxy-γ-butyrolactone, (2) addition of methyllithium across the lactone carbonyl, and (3) acid hydrolysis of the acetal moiety. An alternative synthesis consists of the acid-catalyzed conversion of 3,3-dimethoxy-2-hydroxy-2-methyltetrahydrofuran into laurencione methyl ether and subsequent acid-catalyzed hydrolysis. In addition, a convenient synthesis of the coffee and caramel flavor component 2-methyl- 3(2H)-furanone has been developed by acid-catalyzed rearrangement of 2- methoxy-2-methyltetrahydrofuran-3-one.
