70 results match your criteria synthesis oxazolidin-2-ones


Chemodivergent Synthesis of Oxazolidin-2-ones via Cu-Catalyzed Carboxyl Transfer Annulation of Propiolic Acids with Amines.

J Org Chem 2021 12 2;86(23):16940-16947. Epub 2021 Nov 2.

College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620, China.

Carboxylic acids are widely found in natural products and bioactive molecules and have served as raw material compounds in industry. We now report the first example of copper(I)-catalyzed carboxyl transfer annulation of propiolic acids with amines, thereby chemodivergently constructing the oxazolidine-2-ones. In this reaction, two kinds of key propargyamine intermediates were formed through sequential CuI/NBS-catalyzed oxidative deamination/decarboxylative alkynylation or CuI-catalyzed decarboxylative hydroamination/alkynylation. Read More

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December 2021

Non-precious metal carbamates as catalysts for the aziridine/CO coupling reaction under mild conditions.

Dalton Trans 2021 Apr;50(15):5351-5359

Dipartimento di Chimica e Chimica Industriale, University of Pisa, Via G. Moruzzi 13, I-56124 Pisa, Italy. and CIRCC, via Celso Ulpiani 27, I-70126 Bari, Italy.

The catalytic potential of a large series of easily available metal carbamates (based on thirteen different non-precious metal elements) was explored for the first time in the coupling reaction between 2-aryl-aziridines and carbon dioxide, working under solventless and ambient conditions and using tetraalkylammonium halides as co-catalysts. The straightforward synthesis of novel [NbCl3(O2CNEt2)2], NbCl, and [NbBr3(O2CNEt2)2], NbBr, is reported. The niobium complex NbCl, in combination with NBu4I, emerged as the best catalyst of the overall series to convert aziridines with small N-alkyl substituents into the corresponding 5-aryl-oxazolidin-2-ones. Read More

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Stereoselective Synthesis of Oxazolidin-2-Ones via an Asymmetric Aldol/Curtius Reaction: Concise Total Synthesis of (-)-Cytoxazone.

Molecules 2021 Jan 23;26(3). Epub 2021 Jan 23.

Department of Chemistry, The Catholic University of Korea, Bucheon 14662, Korea.

Herein, we are reporting an efficient approach toward the synthesis of 4,5-disubstituted oxazolidin-2-one scaffolds. The developed approach is based on a combination of an asymmetric aldol and a modified Curtius protocol, which uses an effective intramolecular ring closure to rapidly access a range of oxazolidin-2-one building blocks. This strategy also permits a straightforward and concise asymmetric total synthesis of (-)-cytoxazone. Read More

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January 2021

Pyranoid Spirosugars as Enzyme Inhibitors.

Curr Org Synth 2020 Sep 24. Epub 2020 Sep 24.

Department of Biotechnology and Bioscience, University of Milano-Bicocca, Milan. Italy.

Background: Pyranoid spirofused sugar derivatives represent a class of compounds with a significant impact in the literature. Under the structural point of view, the rigidity inferred by the spirofused entity has made these compound object of interest mainly as enzymatic inhibitors, in particular of carbohydrate processing enzymes among which glycogen phosphorylase and sodium glucose co-transporter 2, important target enzymes for diverse pathological states. Most of the developed compounds present the spirofused entity at the C1 position of the sugar moiety, nevertheless spirofused entities can also be found at other sugar ring positions. Read More

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September 2020

A One-Pot Iodo-Cyclization/Transition Metal-Catalyzed Cross-Coupling Sequence: Synthesis of Substituted Oxazolidin-2-ones from -Boc-allylamines.

Org Lett 2020 May 28;22(10):3870-3874. Epub 2020 Apr 28.

Molecular, Macromolecular Chemistry and Materials, ESPCI Paris, PSL University, CNRS, 75005 Paris, France.

A one-pot iodo-cyclization/transition metal-catalyzed cross-coupling sequence is reported to access various C5-functionalized oxazolidin-2-ones from unsaturated Boc-allylamines. Depending on the Grignard reagents used for the cross-coupling, e.g. Read More

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The Synthesis of Functionalized 3-Aryl- and 3-Heteroaryloxazolidin-2-ones and Tetrahydro-3-aryl-1,3-oxazin-2-ones via the Iodocyclocarbamation Reaction: Access to Privileged Chemical Structures and Scope and Limitations of the Method.

J Org Chem 2020 05 5;85(10):6323-6337. Epub 2020 May 5.

Department of Chemistry and Biochemistry, Calvin University, 1726 Knollcrest Circle SE, Grand Rapids, Michigan 49546, United States.

3-Aryl- and 3-heteroaryloxazolidin-2-ones, by virtue of the diverse pharmacologic activities exhibited by them after subtle changes to their appended substituents, are becoming increasingly important and should be considered privileged chemical structures. The iodocyclocarbamation reaction has been extensively used to make many 3alkyl-5-(halomethyl)oxazolidin-2-ones, but the corresponding aromatic congeners have been relatively underexplored. We suggest that racemic 3-aryl- and 3-heteroaryl-5-(iodomethyl)oxazolidin-2-ones, readily prepared by the iodocyclocarbamation reaction of N-allylated aryl or heteroaryl carbamates, may be useful intermediates for the rapid preparation of potential lead compounds with biological activity. Read More

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5-(Carbamoylmethylene)-oxazolidin-2-ones as a Promising Class of Heterocycles Inducing Apoptosis Triggered by Increased ROS Levels and Mitochondrial Dysfunction in Breast and Cervical Cancer.

Biomedicines 2020 Feb 18;8(2). Epub 2020 Feb 18.

Department of Pharmacy, Health and Nutritional Sciences, University of Calabria, Via P. Bucci, 87036 Rende (CS), Italy.

Oxazolidinones are antibiotics that inhibit protein synthesis by binding the 50S ribosomal subunit. Recently, numerous worldwide researches focused on their properties and possible involvement in cancer therapy have been conducted. Here, we evaluated in vitro the antiproliferative activity of some 5-(carbamoylmethylene)-oxazolidin-2-ones on MCF-7 and HeLa cells. Read More

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February 2020

[ C]Carbonyl Difluoride-a New and Highly Efficient [ C]Carbonyl Group Transfer Agent.

Angew Chem Int Ed Engl 2020 04 10;59(18):7256-7260. Epub 2020 Mar 10.

Molecular Imaging Branch, National Institute of Mental Health, National Institutes of Health, 10 Center Drive, Bethesda, MD, 20892-1003, USA.

Herein, the synthesis and use of [ C]carbonyl difluoride for labeling heterocycles with [ C]carbonyl groups in high molar activity is described. A very mild single-pass gas-phase conversion of [ C]carbon monoxide into [ C]carbonyl difluoride over silver(II) fluoride provides easy access to this new synthon in robust quantitative yield for labeling a broad range of cyclic substrates, for example, imidazolidin-2-ones, thiazolidin-2-ones, and oxazolidin-2-ones. Labeling reactions may utilize close-to-stoichiometric precursor quantities and short reaction times at room temperature in a wide range of solvents while also showing high water tolerability. Read More

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MnFeO magnetic nanoparticles modified with chitosan polymeric and phosphotungstic acid as a novel and highly effective green nanocatalyst for regio- and stereoselective synthesis of functionalized oxazolidin-2-ones.

Mater Sci Eng C Mater Biol Appl 2019 Dec 24;105:110109. Epub 2019 Aug 24.

Department of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, Iran. Electronic address:

A novel magnetically recoverable acid nanocatalyst, MnFeO/chitosan/phosphotungstic acid ([email protected]@PTA), was successfully synthesized. The synthesized nanoparticle was studied as the heterogenous nanocatalyst to prepare the functionalized oxazolidin-2-ones as versatile chiral synthons in asymmetrically synthesizing the compounds with biological activity through the reaction of α-epoxyketones with urea and thiourea. This new procedure has notable advantages such as excellent yields, green reaction conditions, and short reaction time. Read More

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December 2019

Stereocontrolled Synthesis of trans/ cis-2,3-Disubstituted Cyclopropane-1,1-diesters and Applications in the Syntheses of Furanolignans.

J Org Chem 2018 10 28;83(20):12549-12558. Epub 2018 Sep 28.

Key Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science , Anhui Normal University , Wuhu , Anhui 241000 , China.

A new Michael addition/intramolecular alkylation sequence of ( Z)-3-(2-bromo-3-arylacryloyl)oxazolidin-2-ones and malonates was developed. By a simple switch of the reaction conditions including the base promoter, solvent, and reaction temperature, both of the cis- and trans-isomers of a series of oxazolidinone-containing 2,3-disubstituted cyclopropane-1,1-diesters could be obtained in good-to-excellent yields and with an excellent diastereoselectivity. The utility of the cyclopropane products was demonstrated in the diastereoselective syntheses of (±)-urinaligran and a stereoisomer of (±)-virgatusin involving the AlCl-promoted [3+2] annulation with veraldehyde or piperonal as the key step. Read More

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October 2018

Stereoselective Synthesis of Highly Substituted Tetrahydropyrans through an Evans Aldol-Prins Strategy.

J Org Chem 2018 08 6;83(16):9039-9066. Epub 2018 Aug 6.

Instituto Universitario de Bio-Orgánica "Antonio González" (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Departamento de Química Orgánica , Universidad de La Laguna (ULL) , Avda. Astrofísico Francisco Sánchez 2 , 38206 San Cristóbal de La Laguna , Tenerife , Spain.

A direct and general method for the synthesis of naturally occurring 2,3,4,5,6-pentasubstituted tetrahydropyrans has been developed, employing β,γ-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 σ bonds and five contiguous stereocenters were straightforwardly generated, and a two-step version, which additionally permitted the isolation of β,γ-unsaturated alcohol precursors bearing an N-acyl oxazolidin-2-one in the α 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. Read More

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Synthesis, Spectroscopic Characterization, and Antibacterial Evaluation of Novel Functionalized Sulfamidocarbonyloxyphosphonates.

Molecules 2018 07 10;23(7). Epub 2018 Jul 10.

Laboratory of Applied Organic Chemistry, Synthesis of Biomolecules and Molecular Modelling Group, Badji-Mokhtar-Annaba University, Box 12, 23000 Annaba, Algeria.

Several new sulfamidocarbonyloxyphosphonates were prepared in two steps, namely carbamoylation and sulfamoylation, by using chlorosulfonyl isocyanate (CSI), α-hydroxyphosphonates, and various amino derivatives and related (primary or secondary amines, β-amino esters, and oxazolidin-2-ones). All structures were confirmed by ¹H, C, and P NMR spectroscopy, IR spectroscopy, and mass spectroscopy, as well as elemental analysis. Eight compounds were evaluated for their antibacterial activity against four reference bacteria including Gram-positive (ATCC 25923), and Gram-negative (ATCC 25922), (ATCC 700603), (ATCC 27853), in addition to three clinical strains of each studied bacterial species. Read More

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Glucosinolate turnover in Brassicales species to an oxazolidin-2-one, formed via the 2-thione and without formation of thioamide.

Phytochemistry 2018 Sep 7;153:79-93. Epub 2018 Jun 7.

Council for Agricultural Research and Economics, Research Centre for Cereal and Industrial Crops, Via di Corticella 133, 40128, Bologna, Italy.

Glucosinolates are found in plants of the order Brassicales and hydrolyzed to different breakdown products, particularly after tissue damage. In Barbarea vulgaris R.Br. Read More

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September 2018

Synthesis of Oxazolidin-2-ones from Unsaturated Amines with CO by Using Homogeneous Catalysis.

Chem Asian J 2018 Sep 24;13(17):2292-2306. Epub 2018 Jul 24.

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, 29, Wangjiang Road, Chengdu, 610064, P. R. China.

Carbon dioxide (CO ), a well-known greenhouse gas, is also a nontoxic, readily accessible, and renewable one-carbon (C1) source. However, owing to its thermodynamic stability and kinetic inertness, the efficient utilization of CO is challenging. Much effort has been devoted to achieving efficient and selective organic transformations of CO . Read More

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September 2018

Design, synthesis and biological activity of 3-pyrazine-2-yl-oxazolidin-2-ones as novel, potent and selective inhibitors of mutant isocitrate dehydrogenase 1.

Bioorg Med Chem 2017 12 13;25(24):6379-6387. Epub 2017 Oct 13.

Department of Pharmaceutical Engineering & Department of Biochemical Engineering, China Pharmaceutical University, 639 Longmian Avenue, Nanjing 211198, China; Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, China. Electronic address:

Isocitrate dehydrogenases (IDHs) catalyze the oxidative decarboxylation of isocitrate to alpha-ketoglutarate (α-KG) generating carbon dioxide and NADPH/NADH. Evidence suggests that the specific mutations in IDH1 are critical to the growth and reproduction of some tumor cells such as gliomas and acute myeloid leukemia, emerging as an attractive antitumor target. In order to discovery potent new mutant IDH1 inhibitors, we designed, synthesized and evaluated a series of allosteric mIDH1 inhibitors harboring the scaffold of 3-pyrazine-2-yl-oxazolidin-2-ones. Read More

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December 2017

Discovery of 3,5-Diphenyl-4-methyl-1,3-oxazolidin-2-ones as Novel, Potent, and Orally Available Δ-5 Desaturase (D5D) Inhibitors.

J Med Chem 2017 11 31;60(21):8963-8981. Epub 2017 Oct 31.

Pharmaceutical Research Division, Takeda Pharmaceutical Company Limited , 26-1, Muraoka-Higashi 2-chome, Fujisawa, Kanagawa 251-8555, Japan.

The discovery and optimization of Δ-5 desaturase (D5D) inhibitors are described. Investigation of the 1,3-oxazolidin-2-one scaffold was inspired by a pharmacophore model constructed from the common features of several hit compounds, resulting in the identification of 3,5-diphenyl-1,3-oxazolidin-2-one 5h as a novel lead showing potent in vitro activity. Subsequent optimization focused on the modification of two metabolic sites, which provided (4S,5S)-5i, a derivative with improved metabolic stability. Read More

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November 2017

Optimization of 3-Pyrimidin-4-yl-oxazolidin-2-ones as Allosteric and Mutant Specific Inhibitors of IDH1.

ACS Med Chem Lett 2017 Feb 16;8(2):151-156. Epub 2016 Dec 16.

Novartis Institutes for Biomedical Research , 250 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.

High throughput screening and subsequent hit validation identified 4-isopropyl-3-(2-((1-phenylethyl)amino)pyrimidin-4-yl)oxazolidin-2-one as a potent inhibitor of IDH1. Synthesis of the four separate stereoisomers identified the (,)-diastereomer (, ) as the most potent isomer. This also showed reasonable cellular activity and excellent selectivity vs IDH1. Read More

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February 2017

(Enantio)selective Hydrogen Autotransfer: Ruthenium-Catalyzed Synthesis of Oxazolidin-2-ones from Urea and Diols.

Angew Chem Int Ed Engl 2016 06 13;55(27):7826-30. Epub 2016 Apr 13.

Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059, Rostock, Germany.

A novel strategy for the synthesis of oxazolidin-2-ones from vicinal diols and urea is described. In this heterocycle synthesis, two different C-O and C-N bonds are sequentially formed in a domino process consisting of nucleophilic substitution and alcohol amination. The use of readily available starting materials and the good atom economy render this process environmentally benign. Read More

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Synthesis of Oxazolidin-2-ones by Oxidative Coupling of Isonitriles, Phenyl Vinyl Selenone, and Water.

Chemistry 2016 Feb 8;22(7):2278-81. Epub 2016 Jan 8.

Laboratory of Synthesis and Natural Products, école Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.

Reaction of alkyl isocyanides, phenyl vinyl selenone, and water in the presence of a catalytic amount of Cs2 CO3 afforded oxazolidin-2-ones in good yields. This unprecedented heteroannulation process created four chemical bonds in a single operation with the isocyano group acting formally as a polarized double bond and phenyl vinyl selenone as a latent 1,3-dipole. The phenylselenonyl group played a triple role as an electron-withdrawing group to activate the 1,4-addition, a leaving group, and a latent oxidant in this transformation. Read More

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February 2016

Cinchona Alkaloid Catalyzed Sulfa-Michael Addition Reactions Leading to Enantiopure β-Functionalized Cysteines.

J Org Chem 2015 Nov 21;80(21):10561-74. Epub 2015 Oct 21.

Van't Hoff Institute for Molecular Sciences, Faculty of Science, The University of Amsterdam , Science Park 904, 1098 XH Amsterdam, The Netherlands.

Sulfa-Michael additions to α,β-unsaturated N-acylated oxazolidin-2-ones and related α,β-unsaturated α-amino acid derivatives have been enantioselectively catalyzed by Cinchona alkaloids functionalized with a hydrogen bond donating group at the C6' position. The series of Cinchona alkaloids includes known C6' (thio)urea and sulfonamide derivatives and several novel species with a benzimidazole, squaramide or a benzamide group at the C6' position. The sulfonamides were especially suited as bifunctional organocatalysts as they gave the products in very good diastereoselectivity and high enantioselectivity. Read More

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November 2015

Intermolecular reductive coupling of esters with benzophenones by low-valent titanium: synthesis of diarylmethyl ketones revisited.

J Org Chem 2015 Apr 17;80(7):3496-503. Epub 2015 Mar 17.

Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101, Koyama-cho Minami, Tottori 680-8552, Japan.

The reductive coupling of aliphatic esters with benzophenones by Zn-TiCl4 in THF gave two- and four-electron reduced products, diaryl(hydroxy)methyl ketones, and diarylmethyl ketones selectively by controlling the reaction conditions. In the reaction of aromatic esters with benzophenones, diarylmethyl ketones were obtained as the sole products. N-(Alkoxycarbonyl)-(S)-α-amino acid methyl esters gave optically active diphenylmethyl ketones by reduction with benzophenone. Read More

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A novel one-pot and one-step microwave-assisted cyclization-methylation reaction of amino alcohols and acetylated derivatives with dimethyl carbonate and TBAC.

ScientificWorldJournal 2014 14;2014:634935. Epub 2014 Oct 14.

Centro de Graduados e Investigación en Química del Instituto Tecnológico de Tijuana, Boulevard Alberto Limón Padilla S/N 22510 Tijuana, BC, Mexico.

A simple and efficient microwave-assisted methodology for the synthesis of 4-substituted-3-methyl-1,3-oxazolidin-2-ones from amino alcohols catalyzed by a ionic liquid was developed. This novel one-pot and one-step cyclization-methylation reaction represents an easier and faster method than any other reported protocols that can be used to obtain the desired products in good yields and high purity. Applying microwave irradiation at 130°C in the presence of TBAC, dimethyl carbonate acts simultaneously as carbonylating and methylating agent and surprisingly promotes an in situ basic trans esterification when a N-acetylated amino alcohol is used as starting material. Read More

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October 2015

Stereoselective aminoxylation of biradical titanium enolates with TEMPO.

Chemistry 2014 Aug 7;20(32):10153-9. Epub 2014 Jul 7.

Departament de Química Orgànica, Universitat de Barcelona, Carrer Martí i Franqués 1-11, 08028 Barcelona, Catalonia (Spain), Fax: (+34) 93-3397878.

A highly efficient and straightforward aminoxylation of titanium(IV) enolates from (S)-N-acyl-4-benzyl-5,5-dimethyl-1,3-oxazolidin-2-ones with TEMPO has been developed. A wide array of functional groups on the acyl moiety, including alkyl and aryl substituents, olefins, esters, or α-cyclopropyl, as well as α-trifluoromethyl groups, are well tolerated. This transformation can therefore produce the α-aminoxylated adducts in excellent yields with high diastereomeric ratios (d. Read More

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Electroreductive coupling of optically active α,β-unsaturated carbonyl compounds with diaryl ketones: asymmetric synthesis of 4,5,5-trisubstituted γ-butyrolactones.

Org Lett 2014 Jun 5;16(12):3348-51. Epub 2014 Jun 5.

Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University , 4-101, Koyama-cho Minami, Tottori 680-8552, Japan.

The electroreductive coupling of optically active N-E-crotonoyl- and N-cinnamoylimidazolidin-2-ones and oxazolidin-2-ones with diaryl ketones in the presence of chlorotrimethylsilane gave adducts with high diastereoselectivity. The adducts were readily transformed to optically active 4,5,5-trisubstituted γ-butyrolactones by treatment with TBAF. Read More

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Synthesis of all four stereoisomers of 5-formyl-4-hydroxymethyl-1,3-oxazolidin-2-ones from D-glucosamine.

Authors:
Teiichi Murakami

Carbohydr Res 2013 Jun 25;375:47-54. Epub 2013 Apr 25.

Biomedical Research Institute, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 6, Tsukuba, Ibaraki, Japan.

All four stereoisomers of 5-formyl-4-hydroxymethyl-1,3-oxazolidin-2-ones (FHOs) were conveniently prepared from D-glucosamine by base-catalyzed epimerizations. 2-N,3-O-Carbonyl-D-glucosamine (7) was successively treated with NaBH4 and NaIO4 to give (4S,5R)-FHO 18, which was epimerized with DBU in DMF to give (4S,5S)-FHO 20. The glucosamine derivative 7 was epimerized to 2-N,3-O-carbonyl-D-mannosamine 23, from which (4R,5R)- and (4R,5S)-FHO derivatives (27 and 31) were prepared. Read More

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Palladium-catalyzed cyclization reactions of 2,3-allenyl amines with propargylic carbonates.

Org Lett 2012 May 26;14(9):2312-5. Epub 2012 Apr 26.

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, PR China.

A highly efficient and atom-economic route to synthesize 5-(1,3,4-alkatrien-2-yl)oxazolidin-2-ones via palladium-catalyzed cyclization reactions of 2,3-allenyl amines with propargylic carbonates was reported. The CO(2) generated in situ from propargylic carbonates is incorporated into the oxazolidin-2-one unit with high efficiency, affording the products in 70-92% yields. Read More

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Novel desosamine-modified 14- and 15-membered macrolides without antibacterial activity.

Bioorg Med Chem Lett 2012 May 29;22(10):3527-30. Epub 2012 Mar 29.

GlaxoSmithKline Research Centre Zagreb, Zagreb, Croatia.

Novel modifications of the desosamine sugar of 14- and 15-membered antibacterial macrolides, in which the desosamine was fused with N-substituted-1,3-oxazolidin-2-ones, were developed in order to completely suppress antibacterial activity and make them promising agents for other biological targets. The synthesis of such bicyclic desosamine derivatives, especially 1,3-oxazolidin-2-one formation, was optimized and conducted under mild conditions without a need for protection/deprotection steps for other functional groups. A focused series of novel desosamine-modified macrolide derivatives was prepared and their antibacterial activities tested. Read More

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Highly efficient asymmetric Michael addition of diaryl phosphine oxides to α,β-unsaturated N-acylated oxazolidin-2-ones.

Chem Asian J 2012 May 13;7(5):881-3. Epub 2012 Mar 13.

Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 P. R. China.

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Stereoselective intramolecular cyclization to 4-(hydroxymethyl)-3-(1H-indolyl)oxazolidin-2-ones.

Chirality 2012 Apr 17;24(4):345-8. Epub 2012 Feb 17.

Dipartimento di Chimica A. M. Tamburro, Università degli Studi della Basilicata, Via dell'Ateneo Lucano 10, 85100, Potenza, Italy.

A simple high-yield three-steps route to optically active 4-hydroxymethyl-3-(1H-indolyl)oxazolidin-2-ones from (S)-glycidol is described. The key intermediates (R)-oxiran-2-ylmethyl 1H-indol-4/-5-ylcarbamates are obtained in high yields from (S)-glycidol. These are readily transformed to oxazolidin-2-ones, very interesting building blocks in drug synthesis. Read More

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Expedient synthesis of pseudo-Pro-containing peptides: towards constrained peptidomimetics and foldamers.

Org Biomol Chem 2012 Mar 8;10(11):2307-17. Epub 2012 Feb 8.

Department of Chemistry G. Ciamician, University of Bologna, via Selmi 2, 40126 Bologna, Italy.

The reaction of sulfonyl peptides containing L- or D-configured Ser or Thr with bis(succinimidyl) carbonate in the presence of a catalytic amount of a base affords, in solution or in the solid phase, the corresponding peptides with one or two, consecutive or alternate oxazolidin-2-ones (Oxd). The Oxd ring can be regarded to as a pseudo-Pro with an exclusively trans conformation of the preceding peptide bond; homochiral Oxd-containing peptides adopt extended conformations, while the presence of a D-configured Oxd favours folded conformations. Read More

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