Silver(I) Carbonate on Celite

Fétizon, M.; Li, Yiming; Jiang, Xuefeng

doi:10.1002/047084289x.rs014.pub2

Cited by 3 publications

(4 citation statements)

References 99 publications

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“…In comparison with the direct alkylation method, this two-step aldol/deoxygenation approach offered an overall more superior outcome in the preparation of 13 . With 13 in hand, the chiral auxiliary was removed under reductive conditions with NaBH 4 to give alcohol 15 (86%), which then underwent modified Lemieux–Johnson and Fétizon oxidations to afford chiral lactone 16 in 85% over 2 steps. Overall, chiral lactone 16 was prepared in 45% via six steps from 4-pentenoic acid, five steps shorter than a previous published route .…”

Section: Results and Discussionsupporting

confidence: 65%

Total Asymmetric Synthesis and Stereochemical Confirmation of (+)- and (−)-Lyoniresinol and Its Deuterated Analogues

2022

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Lyoniresinol and its derivatives are lignans which have been isolated from a plethora of plant species. In addition to exhibiting a range of interesting biological activities including anticancer, anti-inflammatory, antimicrobial, and others, these compounds have also been discovered in wines and spirits and shown to have gustatory effects in these alcoholic matrices. (+)-Lyoniresinol 1 is reported to impart a strong bitter taste while its enantiomer (−)-lyoniresnol 2 is tasteless. The first total asymmetric synthesis of both natural enantiomers (+)-1 and (−)-2 and their deuterated analogues (D 4 )-(+)-3 and (D 4 )-(−)-4 has been achieved, confirming the structure and stereochemistry of the natural products. The synthesized compounds can be utilized as internal standards in stable isotope dilution analysis for improving and optimizing the existing lyoniresinol quantitation methods in the future.

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Section: Results and Discussionsupporting

confidence: 65%

Total Asymmetric Synthesis and Stereochemical Confirmation of (+)- and (−)-Lyoniresinol and Its Deuterated Analogues

2022

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“… 10 Again, the 1,2-diol functionality within 11 proved to be sensitive toward most oxidation conditions, with oxidative cleavage of the C11–C12 bond proving facile (see the SI ). Even the employment of Fetizon’s reagent (silver(I) carbonate on Celite) 19 —commonly used in oxidative lactonization protocols—failed to afford the desired lactone 20 . Extensive screening of conditions revealed that TEMPO-mediated oxidations were the most effective procedures to give 20 : using 1,3-diiodo-5,5-dimethylhydantoin (DIH) as the terminal oxidant, the desired lactone could be obtained in good yield (81% on gram scale), although the efficiency of the oxidation was lower on the decagram scale.…”

Section: Resultsmentioning

confidence: 99%

“…The reaction provided crystalline triol 11, 10 Again, the 1,2-diol functionality within 11 proved to be sensitive toward most oxidation conditions, with oxidative cleavage of the C11−C12 bond proving facile (see the SI). Even the employment of Fetizon's reagent (silver(I) carbonate on Celite)19 commonly used in oxidative lactonization protocolsfailed to afford the desired lactone 20. Extensive screening of conditions a Yields determined by 1 H NMR analysis using MeNO 2 as the internal standard.…”

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confidence: 99%

Asymmetric Total Synthesis of (−)-Phaeocaulisin A

2022

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The therapeutic properties of Curcuma (ginger and turmeric’s family) have long been known in traditional medicine. However, only recently have guaiane-type sesquiterpenes extracted from Curcuma phaeocaulis been submitted to biological testing, and their enhanced bioactivity was highlighted. Among these compounds, phaeocaulisin A has shown remarkable anti-inflammatory and anticancer activity, which appears to be tied to the unique bridged acetal moiety embedded in its tetracyclic framework. Prompted by the promising biological profile of phaeocaulisin A and by the absence of a synthetic route for its provision, we have implemented the first enantioselective total synthesis of phaeocaulisin A in 17 steps with 2% overall yield. Our route design builds on the identification of an enantioenriched lactone intermediate, tailored with both a ketone moiety and a conjugated alkene system. Taking advantage of the umpolung carbonyl-olefin coupling reactivity enabled by the archetypal single-electron transfer (SET) reductant samarium diiodide (SmI 2 ), the lactone intermediate was submitted to two sequential SmI 2 -mediated cyclizations to stereoselectively construct the polycyclic core of the natural product. Crucially, by exploiting the innate inner-sphere nature of carbonyl reduction using SmI 2 , we have used a steric blocking strategy to render sites SET-unreceptive and thus achieve chemoselective reduction in a complex substrate. Our asymmetric route enabled elucidation of the naturally occurring isomer of phaeocaulisin A and provides a synthetic platform to access other guaiane-type sesquiterpenes from C. phaeocaulis —as well as their synthetic derivatives—for medicinal chemistry and drug design.

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“…Silver (I) carbonate on Celite was prepared using a method reported by Fétizon [27]. Celite (30.00 g) was added to a solution of AgNO 3 (30.00 g of AgNO 3 in 200 mL of distilled water) and vigorously stirred for 10 min.…”

Section: Silver (I) Carbonate On Celitementioning

confidence: 99%

Determination of 2-Acetyl-1-pyrroline via a Color-Change Reaction Using Chromium Hexacarbonyl

et al. 2022

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At present, there is no colorimetric method for the quantitation of the aroma compound 2-acetyl-1-pyrroline (2AP). A novel colorimetric method was developed for the determination of 2AP content using chromium hexacarbonyl (Cr(CO)6) as a reagent. The reaction of synthetic 2AP with chromium hexacarbonyl reagent solution in the presence of light produced a green product with an absorption maximum (λmax) at 623 nm. GC–MS was used to confirm the color-change reaction, which showed the loss of 2AP after the addition of Cr(CO)6. This novel method enables facile and cost-effective determination of 2AP in fragrant rice. A comparative analysis of fragrant and nonfragrant rice grain extracts showed that no color-change reaction occurred with the nonfragrant rice sample. A limit of detection (LOD) of 2.00 mg L−1 was determined by method validation with an effective linear concentration ranging from 5.00 to 60.00 mg L−1 of 2AP. The results obtained using the developed colorimetric method were consistent with those obtained by automated static headspace gas chromatography with nitrogen-phosphorus detection (SHS-GC–NPD).

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Silver(I) Carbonate on Celite

Cited by 3 publications

References 99 publications

Total Asymmetric Synthesis and Stereochemical Confirmation of (+)- and (−)-Lyoniresinol and Its Deuterated Analogues

Total Asymmetric Synthesis and Stereochemical Confirmation of (+)- and (−)-Lyoniresinol and Its Deuterated Analogues

Asymmetric Total Synthesis of (−)-Phaeocaulisin A

Determination of 2-Acetyl-1-pyrroline via a Color-Change Reaction Using Chromium Hexacarbonyl

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