10.1021/ol200312q
The research focuses on the rapid construction of the [5-6-7] tricyclic ring skeleton of Calyciphylline alkaloids, specifically targeting Daphnilongeranin B. The study employs a concise photochemical [2+2] cycloaddition-Grob fragmentation sequence to synthesize the common tricyclic ring skeletons found in Calyciphylline A-type alkaloids, including daphnilongeranins, daphniyunnines, and daphniglaucins. The experiments utilize key steps such as Overman rearrangement, Mannich reaction, [2+2] photochemical cycloaddition, and Grob fragmentation. Reactants include (S)-(+)-carvone as the starting material, which is converted through a series of reactions involving CCl3CN, MOMCl, TBSOTf, and other reagents to construct the tricyclic core. The analyses used to confirm the structures and stereochemistry of the synthesized compounds include single crystal X-ray analysis and NMR spectroscopy, with detailed experimental procedures and compound characterization data provided in the supporting information.
10.1021/jo0155254
The study focuses on the synthesis and application of a chiral formyl anion equivalent, specifically lithiated 4-isopropyl-3-(methylthiomethyl)-5,5-diphenyloxazolidin-2-one, for the enantioselective preparation of various chiral compounds, including 1,2-diols, 2-amino alcohols, 2-hydroxy esters, and 4-hydroxy-2-alkenoates. The researchers utilized a series of chemical reactions involving reagents such as BuLi (butyllithium) for lithiation, aldehydes, ketones, and imines for addition reactions, as well as protecting groups like MOMCl (chloromethyl methyl ether) and BnBr (benzyl bromide) for in situ protection of the formed OH groups. The purpose of these chemicals was to achieve selective formation of chiral centers in the target molecules, which are valuable in the synthesis of complex organic molecules and pharmaceuticals. The study also explored the scope and limitations of this new transformation and compared the performance of the chiral auxiliary used with other oxazolidinones of different substitution patterns.
10.1016/j.tet.2007.06.040
The research focuses on the development of a novel nucleoside analogue, specifically 20-deoxy-trans-3',4'-bridged nucleic acids (trans-3',4'-BNA), which feature an S-type sugar conformation. The purpose of this study was to synthesize two new trans-3',4'-BNA monomers from thymidine, with the aim of creating stable duplexes or triplesxes with single- or double-stranded nucleic acids. The research concluded that these novel nucleosides, with their typical S-type sugar conformation, meet the conformational requirements of the B-type DNA duplex, making them strong candidates for ideal DNA structure mimics. The chemicals used in the synthesis process included thymidine, osmium tetroxide, benzyl chloromethyl ether (BOMCl), dibutyltindimethoxide, chloromethyl methyl ether (MOMCl), and various other reagents employed in the protection and deprotection steps, oxidation, reduction, and construction of the trans-fused ring structures. The synthesized nucleosides were confirmed by X-ray crystallography, which indicated their furanose rings had a typical S-type conformation, similar to that observed in the B-type helical structure of the DNA duplex.
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F:Flammable;
