10.1021/jo702573z
The study focuses on the synthesis and structural characterization of novel spirobarbiturates as effective β-turn mimetics, which are important for molecular recognition and signal transduction. The researchers synthesized spirobarbiturates of type III using N-carbamoyl-substituted amino acids and pyrrolidine-1,2,2-tricarboxylic acid derivatives through cyclocondensation reactions. Key chemicals used in the study included N-Boc-protected diethylaminomalonate, 1,3-dibromopropane, and various urea derivatives (e.g., N-carbamoyl glycine, phenylalanine, and tyrosine), which served as building blocks in the synthesis process. The introduction of these compounds aimed to create molecular scaffolds that could be utilized as biomolecular probes to explore binding interactions with target proteins, ultimately contributing to the development of peptide mimetics with potential therapeutic applications.
10.1016/S0040-4039(01)91879-9
The study details the synthesis of 5-acetoxy-9-oxotridecanolactone as a model for erythronolide B, the aglycone of erythromycin B. The researchers aimed to develop a route to 5-acetoxy-13-hydroxy-9-oxotridecanoic acid, with the intention of lactonization at the final stage of macrolide synthesis. The synthesis involved assembling a thirteen-carbon backbone from two cyclopentanoid and one propanoid unit. Key steps included alkylation of the potassio salt of cyclopentanone carboxylic ester with 1,3-dibromopropane, decarboxylation with HBr, Baeyer-Villiger oxidation using CF3CO3H, and further alkylation and decarboxylation steps. The study also involved protecting and unmasking the cyclopentanone carbonyl group, reduction of an ester group with LiAlH4, and oxidation with Collins' reagent. The final lactonization was achieved using p-toluenesulfonyl chloride and Et3N, or alternatively, 1,1'-carbonyldiimidazole and sodium t-amylate. The synthetic route demonstrated potential applicability to erythronolide and other macrolide systems.
10.1055/s-2002-34837
The research presents a facile and efficient approach to synthesize 4-(2-cyanoethylthio)-1,3-dithiole-2-thione (1), a key compound for the preparation of tetrathiafulvalene (TTF) derivatives, from TBA2[Zn(dmit)2]. The study explores the synthetic conditions for preparing compound 1 and uses it to synthesize new electron donors with two TTF units. The chemicals used in the process include TBA2[Zn(dmit)2], 3-bromopropionitrile, pyridine hydrochloride, Hg(OAc)2, and various electrophilic reagents such as 1,2-dibromoethane and 1,3-dibromopropane. The research concludes that compound 1 can be synthesized with high efficiency using four equivalents of an organic ammonium salt, yielding new electron donors with two TTF units, which are significant for the study of organic conductors and molecular spin-ladder systems.