Preparation of Carboxylic Acids from Aldehydes (Including Hydroxylated Benzaldehydes) by Oxidation with Chlorite.

Lindgren, B.; Nilsson, T.; Husebye, Steinar; Mikalsen, Øyvind; Leander, Kurt; Swahn, Carl‐Gunnar

doi:10.3891/acta.chem.scand.27-0888

Cited by 510 publications

(214 citation statements)

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“…Reduction of the orthoquinone monoketal produced 45, which formed the skeleton of 2. Finally, successive benzylation of the hydroxyl group of 45 to provide 46, sodium chlorite-mediated oxidation [61][62][63] of the aldehyde to the corresponding carboxylic acid 47, and complete debenzylation afforded 2. The 1 H and 13 C NMR spectra of 2 were in agreement with those of the natural product; however, subtle differences in chemical shifts were observed (Supplementary Tables 4 and 5).…”

Section: Strategymentioning

confidence: 99%

A unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins

et al. 2014

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Ellagitannins are a family of polyphenols containing more than 1,000 natural products. Nearly 40% of these compounds contain a highly oxygenated diaryl ether that is one of the most critical elements to their structural diversity. Here, we report a unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins. The strategy involves oxa-Michael addition of phenols to an orthoquinone building block, with subsequent elimination and reductive aromatization. The design of the building block-a halogenated orthoquinone monoketal of gallal-reduces the usual instability of orthoquinone and controls addition/elimination. Reductive aromatization is achieved with perfect chemoselectivity in the presence of other reducible functional groups. This strategy enables the synthesis of different diaryl ethers. The first total synthesis of a natural ellagitannin bearing a diaryl ethers is performed to demonstrate that the strategy increases the number of synthetically available ellagitannins.

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Section: Strategymentioning

confidence: 99%

A unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins

et al. 2014

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“…The synthesis involved reaction of 3-bromothiophene-2-carbaldehyde 1 with sodium azide in DMSO to generate an azidothiophene carbaldehyde, 18 which was oxidized using the Lindgren reaction 19 to generate 3-azidothiophene-2-carboxylic acid 2. Steglich esterification 20 gave the azido ester intermediate 3.…”

Section: Ut-b Inhibitor Identification By High-throughput Screeningmentioning

confidence: 99%

Triazolothienopyrimidine Inhibitors of Urea Transporter UT-B Reduce Urine Concentration

Yao

Anderson

Zhang

et al. 2012

Journal of the American Society of Nephrology

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Urea transport (UT) proteins facilitate the concentration of urine by the kidney, suggesting that inhibition of these proteins could have therapeutic use as a diuretic strategy. We screened 100,000 compounds for UT-B inhibition using an optical assay based on the hypotonic lysis of acetamide-loaded mouse erythrocytes. We identified a class of triazolothienopyrimidine UT-B inhibitors; the most potent compound, UTB inh -14, fully and reversibly inhibited urea transport with IC 50 values of 10 nM and 25 nM for human and mouse UT-B, respectively. UTB inh -14 competed with urea binding at an intracellular site on the UT-B protein. UTB inh -14 exhibited low toxicity and high selectivity for UT-B over UT-A isoforms. After intraperitoneal administration of UTB inh -14 in mice to achieve predicted therapeutic concentrations in the kidney, urine osmolality after administration of 1-deamino-8-D-arginine-vasopressin was approximately 700 mosm/kg H 2 O lower in UTB inh -14-treated mice than vehicle-treated mice. UTB inh -14 also increased urine output and reduced urine osmolality in mice given free access to water. UTB inh -14 did not reduce urine osmolality in UT-B knockout mice. In summary, these data provide proof of concept for the potential utility of UT inhibitors to reduce urinary concentration in high-vasopressin, fluid-retaining conditions. The diuretic mechanism of UT inhibitors may complement the action of conventional diuretics, which target sodium transport.

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“…Because isolated yields of the sensitive dialdehyde after column chromatography were mediocre at best, it was decided to use the crude dialdehyde still contaminated with PPh 3 and PPh 3 O directly in the subsequent Pinnick oxidation step. [10,11] Treatment with NaH 2 PO 4 and NaClO 2 while using 2-methyl-2-butene as the HOCl scavenger yielded diacid 16 in 95 % yield over the two steps. Purification of the diacid was achieved by extracting it into the water layer with NaHCO 3 and washing the water layer with EtOAc to remove the PPh 3 , PPh 3 O and other apolar organic residues.…”

Section: Resultsmentioning

confidence: 99%

Attempted [2]Catenane Synthesis via a Quasi[1]catenane by a Templated Backfolding Strategy

et al. 2017

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Preparation of Carboxylic Acids from Aldehydes (Including Hydroxylated Benzaldehydes) by Oxidation with Chlorite.

Cited by 510 publications

References 0 publications

A unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins

A unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins

Triazolothienopyrimidine Inhibitors of Urea Transporter UT-B Reduce Urine Concentration

Attempted [2]Catenane Synthesis via a Quasi[1]catenane by a Templated Backfolding Strategy

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