83402-87-3Relevant academic research and scientific papers
Synthesis and biological evaluation of truncated derivatives of abyssomicin C as antibacterial agents
Monjas, Leticia,Fodran, Peter,Kollback, Johanna,Cassani, Carlo,Olsson, Thomas,Genheden, Maja,Larsson, D. G. Joakim,Wallentin, Carl-Johan
, p. 1468 - 1474 (2019)
The synthesis and antibacterial activity of two new highly truncated derivatives of the natural product abyssomicin C are reported. This work outlines the limits of structural truncation of the natural product and consequently provides insights for furthe
Dynamics in Catalytic Asymmetric Diastereoconvergent (3 + 2) Cycloadditions with Isomerizable Nitrones and α-Keto Ester Enolates
Ezawa, Tetsuya,Sohtome, Yoshihiro,Hashizume, Daisuke,Adachi, Masaya,Akakabe, Mai,Koshino, Hiroyuki,Sodeoka, Mikiko
supporting information, p. 9094 - 9104 (2021/07/01)
Reaction design in asymmetric catalysis has traditionally been predicated on a structurally robust scaffold in both substrates and catalysts, to reduce the number of possible diastereomeric transition states. Herein, we present the stereochemical dynamics in the Ni(II)-catalyzed diastereoconvergent (3 + 2) cycloadditions of isomerizable nitrile-conjugated nitrones with α-keto ester enolates. Even in the presence of multiple equilibrating species, the catalytic protocol displays a wide substrate scope to access a range of CN-containing building blocks bearing adjacent stereocenters with high enantio- and diastereoselectivities. Our computational investigations suggest that the enantioselectivity is governed in the deprotonation process to form (Z)-Ni-enolates, while the unique syn addition is mainly controlled by weak noncovalent bonding interactions between the nitrone and ligand.
A 3 - glyceraldehyde phosphate dehydrogenase inhibitor and its preparation method and application
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Paragraph 0044-0046, (2018/04/20)
The invention provides an inhibitor of glyceraldehyde-3-phosphate dehydrogenase, a preparation method and anticancer application thereof. According to the invention, pharmacological experiments show that the compound has strong killing effect on human col
Chemoselective conversion from α-hydroxy acids to α-keto acids enabled by nitroxyl-radical-catalyzed aerobic oxidation
Furukawa, Keisuke,Inada, Haruki,Shibuya, Masatoshi,Yamamoto, Yoshihiko
supporting information, p. 4230 - 4233 (2016/09/09)
The chemoselective oxidation of α-hydroxy acids to α-keto acids catalyzed by 2-azaadamantane N-oxyl (AZADO), a nitroxyl radical catalyst, is described. Although α-keto acids are labile and can easily release CO2 under oxidation conditions, the use of molecular oxygen as a cooxidant enables the desired chemoselective oxidation.
Construction of 1,2,5-tricarbonyl compounds using methyl cyanoacetate as a glyoxylate anion synthon combined with copper(I) iodide-catalyzed aerobic oxidation
Kim, Se Hee,Kim, Ko Hoon,Kim, Jae Nyoung
, p. 3335 - 3339 (2012/01/19)
A practical and efficient synthesis of various 1,2,5-tricarbonyl compounds is described. The synthesis has been carried out by a conjugate addition of methyl cyanoacetate to the β-position of α,β-unsaturated carbonyl compounds and a subsequent copper(I) iodide-catalyzed aerobic oxidation. In addition, various α-aryl- and α-alkyl-α-keto esters have been synthesized using a similar approach. Copyright
Asymmetrie aerobic oxidation of α-hydroxy acid derivatives by C 4-symmetric, vanadate-centered, tetrakisvanadyl(V) clusters derived from N-salicylidene-α-aminocarboxylates
Chen, Chien-Tien,Bettigeri, Sampada,Weng, Shiue-Shien,Pawar, Vijay D.,Lin, Ya-Hui,Liu, Cheng-Yuan,Lee, Way-Zen
, p. 8175 - 8185 (2008/02/13)
(Chemical Equation Presented) A series of chiral vanadyl(V) methoxides bearing 3-t-butyl-5-substituted N-salicylene-L-valinate and L-t-leucinate as chiral auxiliaries has been prepared. In all cases except the 3,5-di-t-butyl analogue, they exist as monomers both in solution and in the single crystal state. In the case of the 3,5-di-t-butyl analogue, the architectural nature of the vanadyl(V) complex highly depends on the base used during the complex formation event. A pentanuclear C4-symmetric complex was formed when potassium salts were employed instead of the corresponding sodium salts. A central vanadate(V) unit serves to grip four identical chiral monomelic vanadyl(V) units together, by which a potassium ion sits on top of the four flanking units through carbonyl coordinations and serves to hold the whole cluster by cooperation with the central vanadate(V) unit. In comparison with the corresponding monomelic vanadyl(V) methoxide complex, the cluster complex was utilized to facilitate the asymmetric aerobic oxidations of various racemic α-hydroxyesters, -amides, and -thioesters with excellent selectivity factors (krel 40 to >500).
Stereochemical Control in Microbial Reduction. 30. Reduction of Alkyl 2-Oxo-4-phenylbutyrate as Precursors of Angiotensin Converting Enzyme (ACE) Inhibitors
Dao, Duc Hai,Kawai, Yasushi,Hida, Kouichi,Bornes, Sander,Nakamura, Kaoru,Ohno, Atsuyoshi,Okamura, Mutsuo,Akasaka, Takeshi
, p. 425 - 432 (2007/10/03)
Alkyl 2-oxo-4-phenylbutyrates are reduced to the corresponding alkyl (R)-2-hydroxy-4-phenylbutyrates, versatile chiral building blocks in organic synthesis, in high chemical yield (80-90%) with excellent stereoselectivity (>90%ee). The reaction has been run in aqueous diethyl ether at 30 °C for 24 h under the catalysis of bakers' yeast (Saccharomyces cerevisiae) which was preincubated for 6 h in the presence of phenacyl chloride. The amount of water in the medium should be controlled strictly not to exceed 0.8 mL (g yeast)-1.
Pyruvic Acid Dimethylhydrazone. A Synthetic Equivalent of the Pyruvic Acid Dianion
Tapia, Ines,Alcazar, Victoria,Moran, Joaquin R.,Caballero, Cruz,Grande, Manuel
, p. 697 - 700 (2007/10/02)
The pyruvic acid dimethyl hydrazone can be easily prepared in ether.This compound, after deprotonation with alkyllithium, forms a strong nucleophile which on tratment with electrophiles and acidic work up yield α-ketoacids, α-hydroxybutenolides or α,γ-diketoacids.
