New Approach for the Construction of the Coumarin Frame and Application in the Total Synthesis of Natural Products

Jerezano, Alberto V.; Jiménez, Fabiola; Cruz, María del Carmen; Montiel, Luisa E.; Delgado, Francisco; Tamariz, Joaquı́n

doi:10.1002/hlca.201000306

Cited by 44 publications

(18 citation statements)

References 80 publications

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“…Scopoletin (4) was isolated from authentic Noni fruit in our laboratory and its identification was determined by HPLC, mass spectrometry, and nuclear magnetic resonance (purity >99%), by comparison with the literature. [ 18 ]…”

Section: Methodsmentioning

confidence: 99%

Quantitative determination of bioactive constituents in Noni Juice by High-performance liquid chromatography with electrospray ionization triple quadrupole mass spectrometry

Yan

Jiang

et al. 2018

Phcog Mag

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Background:Noni juice has been extensively used as folk medicine for the treatment of arthritis, infections, analgesic, colds, cancers, and diabetes by Polynesians for many years. Due to the lack of standard scientific evaluation methods, various kinds of commercial Noni juice with different quality and price were available on the market.Objective:To establish a sensitive, reliable, and accurate high-performance liquid chromatography with electrospray ionization triple quadrupole mass spectrometry (HPLC-ESI-MS/MS) method for separation, identification, and simultaneous quantitative analysis of bioactive constituents in Noni juice.Materials and Methods:The analytes and eight batches of commercially available samples from different origins were separated and analyzed by the HPLC-ESI-MS/MS method on an Agilent ZORBAX SB-C18 (150 mm × 4.6 mm i.d., 5 μm) column using a gradient elution of acetonitrile-methanol-0.05% glacial acetic acid in water (v/v) at a constant flow rate of 0.5 mL/min.Results:Seven components were identification and all of the assay parameters were within the required limits. Components were within the correlation coefficient values (R2 ≥ 0.9993) at the concentration ranges tested. The precision of the assay method was <0.91% and the repeatability between 1.36% and 3.31%. The accuracy varied from 96.40% to 103.02% and the relative standard deviations of stability were <3.91%. Samples from the same origin showed similar content while different origins showed significant different result.Conclusions:The developed methods would provide a reliable basis and be useful in the establishment of a rational quality control standard of Noni juice.SUMMARY Separation, identification, and simultaneous quantitative analysis method of seven bioactive constituents in Noni juice is originally developed by high-performance liquid chromatography with electrospray ionization triple quadrupole mass spectrometryThe presented method was successfully applied to the quality control of eight batches of commercially available samples of Noni juiceThis method is simple, sensitive, reliable, accurate, and efficient method with strong specificity, good precision, and high recovery rate and provides a reliable basis for quality control of Noni juice. Abbreviations used: HPLC-ESI-MS/MS: High-performance liquid chromatography with electrospray ionization triple quadrupole mass spectrometry, LOD: Limit of detection, LOQ: Limit of quantitation, S/N: Signal-to-noise ratio, RSD: Relative standard deviations, DP: Declustering potential, CE: Collision energy, MRM: Multiple reaction monitoring, RT: Retention time.

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Section: Methodsmentioning

confidence: 99%

Quantitative determination of bioactive constituents in Noni Juice by High-performance liquid chromatography with electrospray ionization triple quadrupole mass spectrometry

Yan

Jiang

et al. 2018

Phcog Mag

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“…[20][21][22]24 In the absence of a Lewis acid, poor or no reaction is observed even at a high temperature. In the synthetic strategy, for the preparation of indoles 1a-p proposed herein (Scheme 2), the last step of the route involves the iodine-assisted cyclization of the key enaminone precursors 3a-p.…”

Section: Resultsmentioning

confidence: 99%

“…2-Bromoacetophenones 6c-d were prepared by bromination of acetophenones 7a-b with N-bromosuccinimide (NBS) in the presence of p-toluenesulfonic acid in good yields (90-95%). 22,24,26 …”

Section: Preparation Of α-Anilinocarbonyl Compounds 4a-pmentioning

confidence: 99%

“…19 Previously, we designed a new method for the preparation of benzofurans, 20 via a cyclization of functionalized enaminones. This strategy was successfully applied to the synthesis of indoles 21 and coumarins 22 (Scheme 1). In order to optimize this methodology, we found that iodine 23 was an efficient promoter in the annulation of the respective enaminones to obtain benzofurans and benzothiophenes.…”

Section: Introductionmentioning

confidence: 99%

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Iodine-mediated one-pot synthesis of indoles and 3-dimethylaminoindoles via annulation of enaminones

Jerezano¹,

Labarrios²,

Jiménez³

et al. 2013

Arkivoc

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The synthesis of 2-carbonylindoles was achieved via a iodine-mediated cyclization of the corresponding enaminone precursors, which were formed by reaction of the -arylaminomethylene carbonyl derivatives with N,N′-dimethylformamide dimethyl acetal (DMFDMA). An alternative and more efficient procedure consisted of a similar cyclization of the enaminones, but under solvent-free and grinding reaction conditions. In another iodine-promoted procedure, 2-carbonyl-3-dimethylaminoindoles were synthesized via a one-pot cascade reaction between the -arylaminomethylene carbonyl derivative and DMFDMA.

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“…Recently, we reported a novel straightforward synthesis of benzo[ b ]furans , through an intramolecular cyclization of properly functionalized enaminones, which was successfully extended to the preparation of indoles and coumarins . With the aim of optimizing and extending our methodology to other kinds of benzo[ b ]heterocycles, we hereby describe the development of alternative conditions for the preparation of benzo[ b ]furans 1 , and the synthesis of benzo[ b ]thiophenes 2 , by using enaminones 3 and 4 as their precursors, respectively (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthetic Approach to Substituted Benzo[b]furans and Benzo[b]thiophenes by Iodine‐Promoted Cyclization of Enaminones

Labarrios

Jerezano

Jiménez

et al. 2013

Journal of Heterocyclic Chem

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An efficient synthetic approach to the substituted benzo[b]furan and benzo[b]thiophene scaffolds by iodine‐mediated cyclization of the corresponding enaminones is described. This protocol was applied to a large series of these latter precursors to afford the respective benzoheterocycles substituted at the C‐2 position by a carbonyl group functionality. A study of the factors that control this process reveals that the reactivity depends on the presence of electron‐donor groups in the aryl ring of the aryloxycarbonylic and arylthiocarbonylic moieties.

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New Approach for the Construction of the Coumarin Frame and Application in the Total Synthesis of Natural Products

Cited by 44 publications

References 80 publications

Quantitative determination of bioactive constituents in Noni Juice by High-performance liquid chromatography with electrospray ionization triple quadrupole mass spectrometry

Quantitative determination of bioactive constituents in Noni Juice by High-performance liquid chromatography with electrospray ionization triple quadrupole mass spectrometry

Iodine-mediated one-pot synthesis of indoles and 3-dimethylaminoindoles via annulation of enaminones

Efficient Synthetic Approach to Substituted Benzo[b]furans and Benzo[b]thiophenes by Iodine‐Promoted Cyclization of Enaminones

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