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alpha-Amino Acids as Chiral Educts for Asymmetric Products. The Synthesis of alpha’-Amino-alpha,beta-ynones

alpha-Amino acid isoxazolidides have been developed as educts for the preparation of optically pure alpha’-amino-alpha,beta-ynones.The alpha-amino acids were first N-protected as their ethoxycarbonyl, tert-butoxycarbonyl, or phenylsulfonyl derivatives.The isoxazolidides then were formed by the simple, high yield acylation of isoxazolidine by in situ generated alpha-amino acid isobutyl carbonic anhydrides.Individual isoxazolidides of L-alpha-N-substituted alanine, phenylalanine, and methionine, when treated with lithium acetylide, lithium (trimethylsilyl)acetylide, or 1-hexynyllithium, gave high yields of the corresponding optically pure alpha,beta-acetylenic ketones.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1282NO – PubChem

 

Simple exploration of 5-(Chloromethyl)oxazolidin-2-one

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Regioselective anodic alpha-methoxylation of 2-oxazolidinone on boron doped diamond in acidic methanol medium

For the first time, anodic methoxylation of 2-oxazolidinone was investigated on boron doped diamond (BDD) in CH3OHH 2SO4 medium. Voltammetric studies reveal that the 2-oxazolidinone gets oxidised at a potential of 1.5 V vs. SCE on the BDD, whereas on the graphite, the anodic oxidation takes place in the potential region of methanol oxidation. Galvanostatic electrolysis results in the formation of 4-methoxy-2-oxazolidinone (MOD) as a single product in high yield on the BDD and multiple products, along with MOD on the graphite. Generation of methoxy radical on the BDD was confirmed by Electron Spin Resonance (ESR) spectroscopy.

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Oxazolidine – Wikipedia,
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Stereoselective Synthesis of Highly Substituted Tetrahydropyrans through an Evans Aldol-Prins Strategy

A direct and general method for the synthesis of naturally occurring 2,3,4,5,6-pentasubstituted tetrahydropyrans has been developed, employing beta,gamma-unsaturated N-acyl oxazolidin-2-ones as key starting materials. The combination of the Evans aldol addition and the Prins cyclization allowed the diastereoselective and efficient generation of the desired oxacycles in two fashions: a one-pot Evans aldol-Prins protocol, in which five new sigma bonds and five contiguous stereocenters were straightforwardly generated, and a two-step version, which additionally permitted the isolation of beta,gamma-unsaturated alcohol precursors bearing an N-acyl oxazolidin-2-one in the alpha position. From these alcohols were also obtained halogenated pentasubstituted tetrahydropyrans as well as 2,3,4,5-tetrasubstituted tetrahydrofurans, shedding light on the mechanism of the process. Computational studies were consistent with the experimental findings, and this innovative Evans aldol-Prins strategy was performed for the preparation of a battery of more than 30 densely substituted tetrahydropyrans, unprecedentedly fused to a 1,3-oxazinane-2,4-dione ring, both in a racemic fashion and in an enantiomeric fashion. These novel molecules were successfully submitted to several transformations to permit simple access to a variety of differently functionalized tetrahydropyrans. Most of these unique molecules were evaluated for their antimicrobial activity against Gram-positive and Gram-negative bacteria and the yeast Candida albicans, and some structure-activity relationships were established.

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Stereoselective Simmons-Smith cyclopropanation of chiral enamides

(Chemical Equation Presented) Efficient and practical access to chiral aminocyclopropanes is secured by the title reaction (see example). Both E and Z enamides undergo the cyclopropanation with high diastereoselectivity (d.r. up to > 95:5). The application of this methodology to the synthesis of biologically significant aminocyclopropanes illustrates the potential of chiral enamides as useful building blocks for stereoselective organic synthesis.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2026NO – PubChem

 

A new application about (R)-Methyl 2-oxooxazolidine-4-carboxylate

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A New Electrophilic Alaninol Synthon. A General Route to Oxazolidinones of D or (R)-2-Amino Alcohols from L-Serine

A new electrophilic alaninol synthon, (S)-4-(4′-tolylsulfonyloxymethyl)oxazolidin-2-one, derived from serine, undergoes nucleophilic displacements with Gilman cuprates and/or Grignard/CuX reagents in high yields to provide (R)-4-substituted oxazolidinones.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1480NO – PubChem

 

New explortion of (S)-4-(4-Aminobenzyl)oxazolidin-2-one

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N-Desmethyltriptans: One pot efficient synthesis of N-methyl-2-5- [substituted- 1H- indole-3-yl]ethanamines

A straightforward and highly improved method to synthesize N-methyl-2-[5-[substituted-lH-indole-3-yl]ethanamines 4-6, which are the metabolites of tryptans 1-3, is reported. The significance of the process is its simplicity and efficiency in isolating the N- desmethyltriptans derivatives as a free base.

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The important role of (R)-4-Benzyl-2-oxazolidinone

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Enantioselective Total Synthesis of Antibiotic CJ-16,264, Synthesis and Biological Evaluation of Designed Analogues, and Discovery of Highly Potent and Simpler Antibacterial Agents

An improved and enantioselective total synthesis of antibiotic CJ-16,264 through a practical kinetic resolution and an iodolactonization reaction to form the iodo pyrrolizidinone fragment of the molecule is described. A series of racemic and enantiopure analogues of CJ-16,264 was designed and synthesized through the developed synthetic technologies and tested against drug-resistant bacterial strains. These studies led to interesting structure-activity relationships and the identification of a number of simpler, and yet equipotent, or even more potent, antibacterial agents than the natural product, thereby setting the foundation for further investigations in the quest for new anti-infective drugs.

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Oxazolidine – Wikipedia,
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Synthesis of anisolylated aspartyl and glutamyl tripeptides

A process has been developed for transforming the beta-carboxyl of aspartate and the gamma-carboxyl of glutamate into anisolyl ketones. These ketones are occasional byproducts in peptide synthesis, resulting from deprotection or resin-removal processes in the presence of anisole as a scavenger. The ketone amino acids have been incorporated in a tripeptide by coupling with CBMIT. During peptide bond formation the keto group of the glutamyl residue required protection, which was provided as the ethylene dithioketal.

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A palladium-catalyzed domino reaction as key step for the synthesis of functionalized aromatic amino acids

A variety of substituted aromatic systems are synthesized by the Catellani reaction. These are used as precursors for novel amino acids with a basic side chain. Georg Thieme Verlag Stuttgart New York.

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Application of 7517-99-9, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 7517-99-9, molcular formula is C4H7NO3, introducing its new discovery.

Antibiotics in the clinical pipeline at the end of 2015

There is growing global recognition that the continued emergence of multidrug-resistant bacteria poses a serious threat to human health. Action plans released by the World Health Organization and governments of the UK and USA in particular recognize that discovering new antibiotics, particularly those with new modes of action, is one essential element required to avert future catastrophic pandemics. This review lists the 30 antibiotics and two beta-lactamase/beta-lactam combinations first launched since 2000, and analyzes in depth seven new antibiotics and two new beta-lactam/beta-lactamase inhibitor combinations launched since 2013. The development status, mode of action, spectra of activity and genesis (natural product, natural product-derived, synthetic or protein/mammalian peptide) of the 37 compounds and six beta-lactamase/beta-lactam combinations being evaluated in clinical trials between 2013 and 2015 are discussed. Compounds discontinued from clinical development since 2013 and new antibacterial pharmacophores are also reviewed.

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Oxazolidine – Wikipedia,
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