Synthesis of 3,4-disubstituted furans via unsaturated cyclic peroxides arising by photooxygenation of 2,3-bis (bromomethyl)-1,3-butadiene and derived exocyclic dienes

Atasoy, Basri; Ozen, Recep

doi:10.1016/s0040-4020(97)00875-2

Cited by 15 publications

(6 citation statements)

References 23 publications

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“…1 H NMR (CDCl 3 ) (400 MHz) δ: 1.35 (s, 18H), 2.87 (t, 4H, J ) 6.4 Hz), 3.43 (q, 4H, J ) 5.9 Hz), 5.18 (br s, 2H), 6.92 (d, 2H, J ) 7.5 Hz), 7. 45 3,4-bis(2-t-Butoxycarbonylaminoethyl)furan (13c). Compound 13c was obtained following the procedure previously described for compound 13b.…”

Section: 6-bis(2-t-butoxycarbonylaminoethyl)pyridine (13b)mentioning

confidence: 99%

“…The synthesis of compounds 3h − m with an aryl containing spacer was accomplished as summarized in Scheme . For the synthesis of intermediates 12a − c , we used commercially available bromides 11a , b and potassium cyanide in the presence of a catalytic amount of 18-crown-6-ether in acetonitrile, while 11c was synthesized starting from 10 using a synthetic procedure employing carbon tetrabromide . Alcohol 10 was obtained as previously described .…”

Section: Chemistrymentioning

confidence: 99%

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Exploiting Protein Fluctuations at the Active-Site Gorge of Human Cholinesterases: Further Optimization of the Design Strategy to Develop Extremely Potent Inhibitors

et al. 2008

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Protein conformational fluctuations are critical for biological functions, although the relationship between protein motion and function has yet to be fully explored. By a thorough bioinformatics analysis of cholinesterases (ChEs), we identified specific hot spots, responsible for protein fluctuations and functions, and those active-site residues that play a role in modulating the cooperative network among the key substructures. This drew the optimization of our design strategy to discover potent and reversible inhibitors of human acetylcholinesterase and butyrylcholinesterase (hAChE and hBuChE) that selectively interact with specific protein substructures. Accordingly, two tricyclic moieties differently spaced by functionalized linkers were investigated as molecular yardsticks to probe the finest interactions with specific hot spots in the hChE gorge. A number of SAR trends were identified, and the multisite inhibitors 3a and 3d were found to be the most potent inhibitors of hBuChE and hAChE known to date.

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Section: 6-bis(2-t-butoxycarbonylaminoethyl)pyridine (13b)mentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Exploiting Protein Fluctuations at the Active-Site Gorge of Human Cholinesterases: Further Optimization of the Design Strategy to Develop Extremely Potent Inhibitors

et al. 2008

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“…The preparation of diene 19 appears in Scheme 4. According to the reported method, [25] commercially available 2,3‐dimethyl‐1,3‐butadiene ( 31 ) was treated with bromine at room temperature, which was followed by reaction with NBS in the presence of (PhCO 2 ) 2 to provide tetrabromide 32 in 64 % yield (>100 g). Treatment of tetrabromide 32 with potassium iodide and sodium thiosulfate at 45 °C provided diiodide 33 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Lignans Based on a Borate‐mediated One‐pot Sequential Suzuki‐Miyaura Coupling of Cyclic Boranes

Sato

Tanaka

2021

Chemistry A European J

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Lignans are a group of polyphenolic phytochemicals that possess a large spectrum of chemical structures and biological activities. Here the syntheses of lignans -anwulignan, burseran, dehydroxycubebin, ruburisandrin B, and sesamin -are achieved based on a borate-mediated one-pot sequential Suzuki-Miyaura coupling of cis-and trans-fused bicyclic boranes, which were prepared by diastereoselective cyclic hydroboration of exo-cyclic diene with cyclopentyl-and thexylboranes, respectively. A one-pot sequential Suzuki-Miyaura coupling of each cyclic borate with various aryl bromides initiated by activation of the cyclic borane with the carbon nucleophile provided 2,3-dibenzylbutane derivatives with different aromatic substituents. Finally, the syntheses of naturally occurring lignans were accomplished in several steps from the products of Suzuki-Miyaura coupling.

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“…Debromination of endoperoxide 65 with zinc-copper couple yields the labile diene 66 which subsequently undergoes a [4+2] cycloaddition reaction with singlet oxygen to give the bicyclic bisendoperoxide 67 [48] In the enantioselective syntheses of all four stereoisomers of yingzhaosu C 3 from a hepta-2,6-dienol, the 1,2-dioxane skeleton is constructed in a sequence involving a Sharpless asymmetric epoxidation reaction followed by an acidcatalysed epoxide ring opening/cyclisation process as outlined in Scheme 23 for one of the stereoisomers (+)-3. From spectral data and optical rotation measurements, it was concluded that the natural product is likely to be a mixture of enantiomers with a slight excess of the (+)-form [10].…”

Section: Scheme 15mentioning

confidence: 99%

Recent Advances in the Chemistry of Cyclic Peroxides

McCullough¹,

Nojima

2001

COC

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The well-known antimalarial properties of naturally occurring cyclic peroxides artemisinin (qinghaosu), yingzhaosu A and yingzhaosu C have stimulated the development of new strategies for the synthesis of cyclic peroxides with diverse structures, and the investigation of the chemical transformations and properties of such compounds. In this review, recent progress in the chemistry of mono-and polycyclic organic peroxides with ring sizes of five or greater is highlighted and discussed.

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Synthesis of 3,4-disubstituted furans via unsaturated cyclic peroxides arising by photooxygenation of 2,3-bis (bromomethyl)-1,3-butadiene and derived exocyclic dienes

Cited by 15 publications

References 23 publications

Exploiting Protein Fluctuations at the Active-Site Gorge of Human Cholinesterases: Further Optimization of the Design Strategy to Develop Extremely Potent Inhibitors

Exploiting Protein Fluctuations at the Active-Site Gorge of Human Cholinesterases: Further Optimization of the Design Strategy to Develop Extremely Potent Inhibitors

Synthesis of Lignans Based on a Borate‐mediated One‐pot Sequential Suzuki‐Miyaura Coupling of Cyclic Boranes

Recent Advances in the Chemistry of Cyclic Peroxides

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