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Studies towards the synthesis of (+)-ptilomycalin A; stereoselective N-acyliminium ion coupling reactions to enantiopure C-2 substituted lactams

Highly stereoselective N-acyliminium ion coupling reactions of beta-ketoester derived silyl enol ethers with enantiopure lactams derived from (S)-malic acid are reported. This reaction type is applied in the synthesis of the enantiopure C-2 substituted lactam 27, a plausible intermediate in a projected synthesis of ptilomycalin A.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Thiolates chemically induce redox activation of BTZ043 and related potent nitroaromatic anti-tuberculosis agents

The development of multidrug resistant (MDR) and extensively drug resistant (XDR) forms of tuberculosis (TB) has stimulated research efforts globally to expand the new drug pipeline. Nitroaromatic compounds, including 1,3-benzothiazin-4-ones (BTZs) and related agents, are a promising new class for the treatment of TB. Research has shown that the nitroso intermediates of BTZs that are generated in vivo cause suicide inhibition of decaprenylphosphoryl- beta-d-ribose 2? oxidase (DprE1), which is responsible for cell wall arabinogalactan biosynthesis. We have designed and synthesized novel anti-TB agents inspired from BTZs and other nitroaromatic compounds. Computational studies indicated that the unsubstituted aromatic carbons of BTZ043 and related nitroaromatic compounds are the most electron-deficient and might be prone to nucleophilic attack. Our chemical studies on BTZ043 and the additional nitroaromatic compounds synthesized by us and others confirmed the postulated reactivity. The results indicate that nucleophiles such as thiolates, cyanide, and hydride induce nonenzymatic reduction of the nitro groups present in these compounds to the corresponding nitroso intermediates by addition at the unsubstituted electron-deficient aromatic carbon present in these compounds. Furthermore, we demonstrate here that these compounds are good candidates for the classical von Richter reaction. These chemical studies offer an alternate hypothesis for the mechanism of action of nitroaromatic anti-TB agents, in that the cysteine thiol(ate) or a hydride source at the active site of DprE1 may trigger the reduction of the nitro groups in a manner similar to the von Richter reaction to the nitroso intermediates, to initiate the inhibition of DprE1.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Selective hydrogenation of lactic acid to 1,2-propanediol over highly active ruthenium-molybdenum oxide catalysts

Modification of Ru/C with a small amount of MoOx (Ru-MoOx/C) enhanced the catalytic activity in the hydrogenation of L-lactic acid to form 1,2-propanediol and maintained high selectivity. The turnover frequency based on the amount of Ru over the optimized Ru-MoOx/C catalyst (Mo/Ru molar ratio=1:16) was 114 h-1 at 393 K, which was about 4 times higher than that over Ru/C. The same effect of MoOx was obtained over Ru-MoOx/SiO2, although Ru-MoOx/SiO2 showed slightly lower activity than that of Ru-MoOx/C. Ru-MoOx/C achieved a high yield of 95 % in 18 h at 393 K and was applicable to various carboxylic acids to provide the corresponding alcohols in high yields. Modification with MoOx also brought about suppression of racemization and (S)-1,2-propanediol was obtained in high enantiomeric excess at 353 K. Based on kinetic analysis and characterization data, such as XRD, TEM, CO adsorption by a volumetric method, FTIR spectroscopy, and X-ray absorption spectroscopy, for Ru-MoOx/C and Ru-MoOx/SiO2, the catalyst structure and reaction mechanism are proposed.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Total Synthesis of Marine Natural Products: Cephalosporolides

Marine-derived species, in particular, fungi, algae, sponges, and coelenterates are fertile grounds for the discovery of biologically and pharmacologically potent compounds. These molecules are structurally unique and possess a wide range of pharmacological activities. The rigid spiroacetal framework, that is, tetrahydro-spirofurofuranones is present in cephalosporolides E, F, H, and I, while the macrolactone structure is exemplified by cephalosporolides B, C, D, G, and J. These marine-derived molecular architectures are appealing to the synthetic community for their stereoselective synthesis. The present review represents a comprehensive overview of all the reported syntheses of these marine-derived molecules.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Therefore, this conceptually novel strategy might open impressive avenues to establish green and sustainable chemistry platforms.In my other articles, you can also check out more blogs about4254-15-3.Product Details of 4254-15-3

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Asymmetric desymmetrization of 2,2?,6,6?-tetrahydroxybiphenyl through annulation with enantiomerically pure bis(mesylate)

(equation presented) 2,2?,6,6?-Tetrahydroxybiphenyl undergoes a facile annulation reaction with bis(mesylate) derived from (S)-1,2-propanediol in the presence of Cs2CO3 to give the corresponding asymmetric desymmetrization product of S axial chirality with exclusive diastereoselectivity. The desymmetrization product can be utilized as a versatile chiral building block in asymmetric synthesis of axially chiral 6,6?-disubstituted 2,2?-biphenyldiols.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Asymmetric syntheses of the sex pheromones of pine sawflies, their homologs and stereoisomers

We describe efficient and flexible enantioselective syntheses of the active enantiomers of the pheromones of pine sawflies, including the species Diprion jingyuanensis, their homologs and, stereoisomers, as well as those identified from the Chinese species Diprion jingyuanensis, i.e., 126. A total of 48 compounds, including acetates 78-101 and propanoates 102-125, have been synthesized. Our general approach towards these compounds originated from the commercially available chirons diethyl (S)- and (R)-malates, as well as ethyl (R)-3-hydroxybutanoate. The Seebach asymmetric methylation was employed in a key step to control additional configuration. Copyright

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Treatment of neurodegenerative diseases

Disclosed are methods for increasing the differentiation of mammalian neuronal cells for purposes of treating neurodegenerative diseases or nerve damage by administration of various compounds including alcohols, diols and/or triols and their analogues.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Homochiral Ketals in Organic Synthesis. Enantioselective Synthesis of (+)-beta-Eudesmol

An enantioselective preparation of (+)-beta-eudesmol employing a diastereoselective Simmons-Smith cyclopropanation is described.Cyclopropanation of a bicyclic enone precursor is directed by use of the corresponding (2S,3S)-2,3-butanediol ketal.The overall yield of (+)-beta-eudesmol (75 percent ee) from racemic 7-carbomethoxy-3,4,5,6,7,8-hexahydronaphthalen-1(2H)-one is 25percent over eight steps

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Novel Compounds as Cannabinoid Receptor Ligands

Disclosed herein are cannabinoid receptor ligands of formula (I) wherein A1 and Rx are as defined in the specification. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also presented.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Semisynthetic Maytansine analogues for the targeted treatment of cancer

Maytansine, a highly cytotoxic natural product, failed as an anticancer agent in human clinical trials because of unacceptable systemic toxicity. The potent cell killing ability of maytansine can be used in a targeted delivery approach for the selective destruction of cancer cells. A series of new maytansinoids, bearing a disulfide or thiol substituent were synthesized. The chain length of the ester side chain and the degree of steric hindrance on the carbon atom bearing the thiol substituent were varied. Several of these maytansinoids were found to be even more potent in vitro than maytansine. The targeted delivery of these maytansinoids, using monoclonal antibodies, resulted in a high, specific killing of the targeted cells in vitro and remarkable antitumor activity in vivo.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate