4538-50-5Relevant academic research and scientific papers
Synthesis of (±)-eusynstyelamide A
Barykina, Olga V.,Snider, Barry B.
, p. 2664 - 2667 (2010)
The synthesis of (±)-eusynstyelamide A has been accomplished in six steps in 13% overall yield from 6-bromoindole, methyl glycidate, and Boc-protected agmatine. If oxygen is carefully excluded from the reaction, the key NaOH-catalyzed aldol dimerization of the α-ketoamide proceeded efficiently to give Boc-protected eusynstyelamide A.
Facile synthesis of glycidates via oxidation of acrylates with aqueous solution of naocl in the presence of ammonium salts
Ochiai, Bungo,Hirano, Taiki
, p. 487 - 493 (2014)
Various glycidates were obtained in high yields via green oxidation of acrylates with aqueous solution of NaOCl in the presence of ammonium salts. The appropriate choice of ammonium salts fitting to the polarity of the substrates and the reaction under slightly basic conditions were essential for efficient reactions.
Synthesis of the fungal macrolide berkeleylactone A and its inhibition of microbial biofilm formation
Schobert, Rainer,Schrey, Hedda,Schriefer, Manuel G.,Stadler, Marc,Zeng, Haoxuan
, p. 4743 - 4751 (2021/06/11)
The fungal macrolide berkeleylactone A was synthesised in 13 steps and 24% yield using (R)-propylene oxide and an asymmetric Noyori hydrogenation of a β-ketoester to install the stereogenic centres. A domino addition-Wittig olefination of a 13-hydroxytetradecanal intermediate with the cumulated ylide Ph3PCCO closed the macrocyle by establishing the α,β-unsaturated ester group, necessary for the attachment of the sidechain thiol via a thia-Michael reaction. The synthetic berkeleylactone A inhibited the formation of Staphylococcus aureus biofilms and showed significant dispersive effects on preformed biofilms of Candida albicans by at least 45% relative to untreated controls at concentrations as low as 1.3 μg mL-1.
Aromatic Donor-Acceptor Interaction-Based Co(III)-salen Self-Assemblies and Their Applications in Asymmetric Ring Opening of Epoxides
Liang, Jian,Soucie, Luke N.,Blechschmidt, Daniel R.,Yoder, Aaron,Gustafson, Addie,Liu, Yu
supporting information, p. 513 - 518 (2019/01/14)
Aromatic donor-acceptor interaction as the driving force to assemble cooperative catalysts is described. Pyrene/naphthalenediimide functionalized Co(III)-salen complexes self-assembled into bimetallic catalysts through aromatic donor-acceptor interactions and showed high catalytic activity and selectivity in the asymmetric ring opening of various epoxides. Control experiments, nuclear magnetic resonance (NMR) spectroscopy titrations, mass spectrometry measurement, and X-ray crystal structure analysis confirmed that the catalysts assembled based on the aromatic donor-acceptor interaction, which can be a valuable noncovalent interaction in supramolecular catalyst development.
Poly(Alkyl Glycidate Carbonate)s as Degradable Pressure-Sensitive Adhesives
Beharaj, Anjeza,Ekladious, Iriny,Grinstaff, Mark W.
supporting information, p. 1407 - 1411 (2019/01/14)
Insertion of CO2 into the polyacrylate backbone, forming poly(carbonate) analogues, provides an environmentally friendly and biocompatible alternative. The synthesis of five poly(carbonate) analogues of poly(methyl acrylate), poly(ethyl acrylate), and poly(butyl acrylate) is described. The polymers are prepared using the salen cobalt(III) complex catalyzed copolymerization of CO2 and a derivatized oxirane. All the carbonate analogues possess higher glass-transition temperatures (Tg=32 to ?5 °C) than alkyl acrylates (Tg=10 to ?50 °C), however, the carbonate analogues (Td≈230 °C) undergo thermal decomposition at lower temperatures than their acrylate counterparts (Td≈380 °C). The poly(alkyl carbonates) exhibit compositional-dependent adhesivity. The poly(carbonate) analogues degrade into glycerol, alcohol, and CO2 in a time- and pH-dependent manner with the rate of degradation accelerated at higher pH conditions, in contrast to poly(acrylate)s.
The asymmetric total synthesis of (+)-salvianolic acid A
Zheng, Yong,Song, Wei-Bin,Xuan, Li-Jiang
supporting information, p. 5047 - 5050 (2016/07/25)
An asymmetric synthesis of (+)-salvianolic acid A with cardioprotective properties, has been accomplished in a convergent manner in eight steps and 10.6% overall yield. This synthesis features an asymmetric addition of organometallics to optically pure 2,3-epoxypropionate in the presence of BF3·Et2O, Ru(III)-catalyzed directed [Formula presented] olefination, and I2-catalyzed isomerization reaction.
NOVEL 3-INDOL SUBSTITUTED DERIVATIVES, PHARMACEUTICAL COMPOSITIONS AND METHODS FOR USE
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Page/Page column 195; 196, (2016/10/04)
A compound of Formula I is provided: or pharmaceutically acceptable enantiomers, salts or solvates thereof. The 5 invention further relates to the use of the compounds of Formula I as TDO2 inhibitors. The invention also relates to the use of the compounds of Formula I for the treatment and/or prevention of cancer, neurodegenerative disorders such as Parkinson's disease, Alzheimer's disease and Huntington's disease, chronic viral infections such as HCV and HIV, depression, and obesity. The invention also 10 relates to a process for manufacturing compounds of Formula I.
Epoxide manufacturing method
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Paragraph 0049-0056, (2016/10/20)
Method for producing epoxides of formula (I), where R stands for an organic group with 1-10 C atoms, by reaction of compounds of formula (II) with an oxidation agent, characterized in that the production takes place continuously in a tube reactor.
Α coccidiosis production of acrylic acid ester
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Paragraph 0048, (2016/12/16)
PROBLEM TO BE SOLVED: To provide a production method with which α-acyloxy acrylate can be obtained at high yield using commodity chemicals as raw materials and which is thereby suitable to be used industrially as a method for producing the α-acyloxy acrylate. SOLUTION: The method for producing the α-acyloxy acrylate includes a process for obtaining the α-acyloxy acrylate, which has a specific structure, using glycidic esters that have a specific structure. COPYRIGHT: (C)2012,JPOandINPIT
A broadly applicable and practical oligomeric (salen)Co catalyst for enantioselective epoxide ring-opening reactions
White, David E.,Tadross, Pamela M.,Lu, Zhe,Jacobsen, Eric N.
supporting information, p. 4165 - 4180 (2014/06/09)
The (salen)Co catalyst (4a) can be prepared as a mixture of cyclic oligomers in a short, chromatography-free synthesis from inexpensive, commercially available precursors. This catalyst displays remarkable enhancements in reactivity and enantioselectivity relative to monomeric and other multimeric (salen)Co catalysts in a wide variety of enantioselective epoxide ring-opening reactions. The application of catalyst 4a is illustrated in the kinetic resolution of terminal epoxides by nucleophilic ring-opening with water, phenols, and primary alcohols; the desymmetrization of meso epoxides by addition of water and carbamates; and the desymmetrization of oxetanes by intramolecular ring opening with alcohols and phenols. The favorable solubility properties of complex 4a under the catalytic conditions facilitated mechanistic studies, allowing elucidation of the basis for the beneficial effect of oligomerization. Finally, a catalyst selection guide is provided to delineate the specific advantages of oligomeric catalyst 4a relative to (salen)Co monomer 1 for each reaction class.
