CuI mediated synthesis of sulfonyl dihydrofurans

Hsueh, Nai‐Chen; Hsiao, Yu‐Ting; Chang, Meng‐Yang

doi:10.1016/j.tet.2017.05.097

Cited by 13 publications

(5 citation statements)

References 90 publications

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“…NaHCO 3 afforded two regioisomer tetrahydrofurans 20 / 21 (63 % yield, ratio 48 : 52) and ent ‐ 20 / ent ‐ 21 (84 % yield, ratio 43 : 57) as single diastereomers, respectively (Scheme 5, Scheme 6). After careful column chromatography and HPLC separation 2‐(iodomethyl) tetrahydrofurans 21 / ent‐ 21 displayed the standard 5‐ exo‐trig substitution pattern in favor of the trans C1/C2 arrangement of the side chains [26a–f] . The formation of the regioisomers 20 / ent‐ 20 indicated a competing 5‐ endo‐trig reaction [26g,h] .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of (+) and (‐)‐Streptomyces coelicolor Butanolide 5 (SCB‐5)

Donges

Hofmann

Brüggemann³

et al. 2021

Eur J Org Chem

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Various 1-(1-hydroxyalkyl) paraconyl alcohols are important signaling molecules within antibiotics production in Streptomyces sp. Intending developing a flexible convergent chemical synthesis of such butanolides, a zwitterionic aza-Claisen rearrangement was chosen as reliable strategy generating the central stereotriad. Reaction of enantiopure N-allyl pyrrolidines and 4-phenylbutenoic acid fluoride delivered defined configured amides displaying the 2,3,1' stereotriads. The configuration was determined by the allyl alcohol moiety indicating a complete remote stereo control. Amide removal by iodolactonization and proceeding reductions, halocyclization and elimination gave key alkylidene tetrahydrofuran derivatives. Stepwise degradation of the olefins through ozonolysis, reductive workup and protecting group removal delivered both enantiomers of the target Streptomyces coelicolor butanolide 5.

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Section: Resultsmentioning

confidence: 99%

Synthesis of (+) and (‐)‐Streptomyces coelicolor Butanolide 5 (SCB‐5)

Donges

Hofmann

Brüggemann³

et al. 2021

Eur J Org Chem

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“…Cu(I) tends to spontaneously oxidize to Cu(II) in solution and thus the oxidized Cu species needs to return back to Cu(I) for sensing of this metal ion, which was attained by iodide (I − ), a reducing agent, in this experiment. 40 The addition of NaI to the probe failed to induce fluorescence emission, indicating that I − is unlikely to be responsible for the fluorescence emission observed here. The probe also showed little fluorescence emission in the presence of other reducing substances (Fe 2+ , dithiothreitol, and cysteine (Cys)) or protein (bovine serum albumin) (Figure S6C).…”

Section: ■ Results and Discussionmentioning

confidence: 64%

“…Only the addition of CuI to the probe led to a strong fluorescence intensity (Figure S6). Cu(I) tends to spontaneously oxidize to Cu(II) in solution and thus the oxidized Cu species needs to return back to Cu(I) for sensing of this metal ion, which was attained by iodide (I – ), a reducing agent, in this experiment . The addition of NaI to the probe failed to induce fluorescence emission, indicating that I – is unlikely to be responsible for the fluorescence emission observed here.…”

Section: Resultsmentioning

confidence: 99%

Chromo-Fluorogenic Rhodamine-Based Amphiphilic Probe as a Selective and Sensitive Sensor for Intracellular Cu(I) in Living Cells

Jeong,

Ha,

Kumar

et al. 2024

ACS Sens.

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Fluorescent probes are widely studied for metal ion detection because of their multiple favorable properties such as high sensitivity and selectivity, quick response, naked eye detection, and in situ monitoring. However, optical probes that can effectively detect the Cu(I) level in cell interiors are rare due to the difficulty associated with selectively and sensitively detecting this metal ion in a cell environment. Therefore, we designed and synthesized three water-soluble probes (1−3) with a 1,3,5-triazine core decorated by three substituents: a hydrophobic alkyl chain, a hydrophilic maltose, and a rhodamine B hydrazine fluorophore. Among the probes, probe 1, which has an octyl chain and a branched maltose group, was the most effective at sensing Cu + in aqueous solution. Upon addition of Cu + , this probe showed a dramatic color change from colorless to pink in daylight and displayed an intense yellow fluorescence emission under 365 nm light. The limit of detection and dissociation constant (K d ) of this probe were 20 nM and 1.1 × 10 −12 M, respectively, which are the lowest values reported to date. The two metal ion-binding sites and the aggregation-induced emission enhancement effect, endowed by the branched maltose group and the octyl chain, respectively, are responsible for the high sensitivity and selectivity of this probe for Cu + detection, as demonstrated by 1 H NMR, dynamic light scattering, and transmission electron microscopy studies. Furthermore, the probe successfully differentiated the Cu(I) level of cancer cells from that of the normal cells. Thus, the probe holds potential for real-time monitoring of Cu(I) level in biological samples and bioimaging of cancer cells.

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“…The development of facile and environmentally benign strategies to furnish sulfonyl motif is of great significance to the future advances of chemistry and pharmaceuticals [1] . β‐keto sulfones represent a significant class of organic sulfonyl compounds and considerable building blocks in the construction of naturally active compounds and other organic compounds, such as lycopodine alkaloids, [2] polyfunctionalized dihydropyrans, [3] tetrahydrofurans, [4] chromans, [5] and pyrroles [6] . In addition, β‐keto sulfones exhibit bioactivities in a wide range of disease areas such as anti‐tumor, [7] anti‐fungal [8] and anti‐bacterial [9] activities, as well as inhibition of 11β‐HSD [10] and antagonism of bacterial quorum sensing [11] .…”

Section: Introductionmentioning

confidence: 99%

K₂S₂O₈‐Mediated Oxysulfonylation of Vinyl Azides with Sodium Sulfinates to Access β‐Keto Sulfones in Water

et al. 2021

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With water as solvent, K2S2O8 mediated facile and efficient synthesis of β‐keto sulfones through oxysulfonylation of vinyl azides with sodium sulfinates is described. The novel procedure has the advantages of being environmentally benign, mild reaction conditions, short reaction time, easy and simple operation, wide tolerance of functional groups, which establish the practical application of this methodology.

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CuI mediated synthesis of sulfonyl dihydrofurans

Cited by 13 publications

References 90 publications

Synthesis of (+) and (‐)‐Streptomyces coelicolor Butanolide 5 (SCB‐5)

Synthesis of (+) and (‐)‐Streptomyces coelicolor Butanolide 5 (SCB‐5)

Chromo-Fluorogenic Rhodamine-Based Amphiphilic Probe as a Selective and Sensitive Sensor for Intracellular Cu(I) in Living Cells

K₂S₂O₈‐Mediated Oxysulfonylation of Vinyl Azides with Sodium Sulfinates to Access β‐Keto Sulfones in Water

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CuI mediated synthesis of sulfonyl dihydrofurans

Cited by 13 publications

References 90 publications

Synthesis of (+) and (‐)‐Streptomyces coelicolor Butanolide 5 (SCB‐5)

Synthesis of (+) and (‐)‐Streptomyces coelicolor Butanolide 5 (SCB‐5)

Chromo-Fluorogenic Rhodamine-Based Amphiphilic Probe as a Selective and Sensitive Sensor for Intracellular Cu(I) in Living Cells

K2S2O8‐Mediated Oxysulfonylation of Vinyl Azides with Sodium Sulfinates to Access β‐Keto Sulfones in Water

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Product

Resources

About

K₂S₂O₈‐Mediated Oxysulfonylation of Vinyl Azides with Sodium Sulfinates to Access β‐Keto Sulfones in Water