SUPPLEMENTARY INFORMATION
|
|
- Brett Waters
- 6 years ago
- Views:
Transcription
1 doi: /nature22309 Chemistry All reagents and solvents were commercially available unless otherwise noted. Analytical LC-MS was carried out using a Shimadzu LCMS-2020 with UV detection monitored between nm using ESI protocol. The column used was Ascentis express C18 with dimensions of 2.1 mm x 50 mm, 2.7 µm, running at 40 C. The flow rate was 1ml/min using a solvent gradient of 5 to 100% B over 1.8 minutes, where A = water (0.05% TFA) and B = acetonitrile (0.05% TFA). Where indicated the mobile phases were made basic and replaced with A= water +6.5 mm NH 4 HCO 3 to ph10 in A, and B = acetonitrile (no additive). An alternative method was employed for some samples using UPLC-MS, which was carried out using a Waters Acquity UPLC and Waters SQD mass spectrometer. In this system, the UV detection was set = nm and mass spectrometry was done with ESI with positive/negative switching and cone voltage = 10 V. The column used was Waters Acquity HSS T3, 1.8µm, 2.1 x30 mm, at temperature 30 C. The flow rate was 1ml/min using a solvent gradient of 2 to 98% B over 1.5 minutes (total runtime with equilibration back to starting conditions 2 min), where A = 0.1% formic acid in water and B = 0.1% formic acid in acetonitrile. For 1 H NMR and 13 C NMR spectroscopy, the chemical shifts are reported in part-permillion from a tetramethylsilane standard. (R)-(4-fluoro-2-propylphenyl)(1H-imidazol-2-yl)methanol (AZ8838). 2-Bromo-4- fluorobenzaldehyde (5.00 g, 24.6 mmol) was added to propylboronic acid (3.25 g, 36.9 mmol), PdCl 2 (dppf) (1.80 g, 2.46 mmol) and Cs 2 CO 3 (16.0 g, 49.3 mmol) in dioxane (40 ml) and water (10 ml), then warmed to 80 C under nitrogen. The resulting suspension was stirred at 80 C for 12 hours. The reaction mixture was diluted with EtOAc (50 ml), and washed sequentially with an aqueous saturated NaCl solution (20 ml x3). The organic layer was dried over Na 2 SO 4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography with an elution gradient 0 to 5% EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford 4-fluoro-2- propylbenzaldehyde (3.10 g, 76 %) as a pale yellow liquid. 1 H NMR (400 MHz, DMSO-d 6 ): δ (s, 1H), 7.93 (dd, 1H, J = 8.2, 6.3), (m, 2H), (m, 2H), 1.58 (m, 2H), 0.93 (t, 3H, J = 7.3). In a separate reaction flask, sodium hydride (0.53 g, 22.0 mmol) in THF (50 ml) was cooled to 0 C over a period of 10 minutes under nitrogen. To this was slowly added imidazole (1.00 g, 14.7 mmol) in THF (30 ml) under nitrogen and the temperature was increased to room temperature gradually (caution: exothermic reaction with liberation of gas). The resulting mixture was stirred at 25 C for 30 minutes, and then (2- (chloromethoxy)ethyl)trimethylsilane (3.67 g, 22.0 mmol) was added slowly to the mixture at 0 C over a period of 1 minute under nitrogen. The temperature was increased to room temperature gradually. The resulting mixture was stirred at 25 C for 14 hours. The mixture was concentrated and diluted with EtOAc (200 ml), and washed with water (150 ml). The organic layer was dried over Na 2 SO 4, filtered and evaporated to afford crude product. The crude product was purified by C18-flash chromatography with an elution gradient 0 to 50% MeCN in water. Pure fractions were evaporated to dryness to afford 1-((2- (trimethylsilyl)ethoxy)methyl)-1h-imidazole (2.91 g, 100%) as a white oil which solidified 1
2 RESEARCH SUPPLEMENTARY INFORMATION on standing. 1 H NMR (300 MHz, DMSO-d 6 ): δ (s, 1H), (s, 1H), (s, 1H), (s, 2H), (m, 2H), (m, 2H), (d, 9H, J = 6.9 Hz); LC-MS: m/z (ES+), [M+H]+ = 199; HPLC t R = min. To a stirred solution of 4-fluoro-2-propylbenzaldehyde (0.30 g, 1.82 mmol) in THF (5 ml) at -78 C, was added a mixture of 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (0.40 g, 2.02 mmol), n-buli (0.26 g, 4.03 mmol) in THF (5 ml) over a period of 1 minute under nitrogen. The resulting solution was stirred at -78 C for 1 hour. The temperature was increased to room temperature over a period of several hours. The reaction mixture was quenched with saturated NH 4 Cl (5 ml), extracted with DCM (3 x 10 ml). The organic layer was dried over Na 2 SO 4, filtered and evaporated to afford a yellow oil. The residue was purified by preparative TLC (EtOAc: petroleum ether = 1: 2), to afford (4-fluoro-2- propylphenyl)(1-((2-(trimethylsilyl)ethoxy)methyl)-1h-imidazol-2-yl)methanol (0.40 g, 54.4 %) as an orange oil. 1 H NMR (300 MHz, CDCl 3 ): δ 7.21 (dd, J = 8.57, 5.93 Hz, 1 H), 7.05 (dd, J = 16.48, 1.41 Hz, 2 H), (m, 2 H), 6.16 (s, 1 H), (m, 2 H), (m, 2 H), (m, 2 H), (m, 2 H), 1.00 (t, J = 7.25 Hz, 3 H), (m, 2 H), (m, 9 H); LC-MS: m/z (ES+), [M+H]+ = 365; HPLC t R = min. To a solution of (4-fluoro-2-propylphenyl)(1-((2-(trimethylsilyl)ethoxy)methyl)-1Himidazol-2-yl)methanol (11.6 g, mmol) in DCM (50 ml) was added TFA (24.5 ml, 318 mmol). The resulting solution was refluxed for 3 hrs and evaporated. The residue was redissolved in DCM (50 ml) and the solution was treated with saturated NaHCO 3. The precipitate was filtered and dried under vacuum to give (4-fluoro-2-propylphenyl)(1Himidazol-2-yl)methanol (5.88 g, 79 %) as an off-white solid. 1 H NMR (300 MHz, DMSOd 6 ): δ (br. s., 1H) 7.51 (dd, J = 8.57, 6.31 Hz, 1H), (m, 4H), 6.00 (d, J = 4.33 Hz, 1H), 5.90 (d, J = 4.33 Hz, 1H), (m, 1H), (m, 1H), (m, 2H), 0.90 (t, J =7.25 Hz, 3H); UPLC-MS: m/z (ES+), [M+H]+ = 235; TFA, HPLC t R = 0.57 min. The racemic material was separated by chiral SFC using a chiralpak AD-H column (30 x 250 mm, 5 µm). The mobile phase A was supercritical CO 2, and Mobile phase B was isopropanol containing 0.1% dimethylamine. A gradient of up to 15% B was run at 2.8 ml/min and two peaks were isolated to give (R)-(4-fluoro-2-propylphenyl)(1H-imidazol-2-yl)methanol (Peak 1 at 3.25 min, g, 33.4 % and > 99%ee, and (S)-(4-fluoro-2-propylphenyl)(1H-imidazol- 2-yl)methanol (Peak 2 at 4.54 min, g, 33.3 % and >99%ee, as white solids. Absolute stereochemistry was assigned based on a crystal structure of the compound with PAR2 receptor. Analytical data for (S)-(4-fluoro-2-propylphenyl)(1H-imidazol-2-yl)methanol: 1 H NMR (400 MHz, DMSO-d 6 ): δ (br. s., 0.5H), 7.49 (dd, J = 8.6, 6.3 Hz, 1H), (m, 4H), 6.85 (br. s., 1H), 6.06 (br. s., 0.5H), 5.88 (s, 1H), (m, 1H), (m, 1H), (m, 2H), 0.87 (t, J =7.25 Hz, 3H); 13 C NMR (100 MHz, DMSO-d 6 ): δ 162.8, 160.4, 150.2, (d, 3 J CF = 6.9 Hz), 137.6, (d, 3 J CF = 6.9 Hz), (d, 1 J CF = 1111 Hz), (d, 2 J CF = 20.7 Hz), (d, 2 J CF = 20.7 Hz), 66.2, 34.1, 23.9, 14.4; HPLC-MS (m/z) [M+H]+ = 235; HPLC t R = 0.57 min; chiral SFC t R = 3.25 min; HRMS (m/z) [M+] calcd for C 13 H 16 FN 2 O; , found
3 RESEARCH (S)-2-(6-bromobenzo[d][1,3]dioxol-5-yl)-N-(4-cyanophenyl)-1-(1-cyclohexylethyl)-1Hbenzo[d]imidazole-5-carboxamide (AZ3451). Cs 2 CO 3 (16.3 g, 50.2 mmol) was added to methyl 4-fluoro-3-nitrobenzoate (5.00 g, 25.1 mmol) and (S)-1-cyclohexylethanamine (4.79 g, 37.6 mmol) in DMF (8 ml) which was cooled to 0 C under nitrogen. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with EtOAc (20 ml), and washed sequentially with saturated NH 4 Cl (15 ml x 2). The aqueous layers were combined and washed with EtOAc (2 x 15 ml). The organic layers were dried Na 2 SO 4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography with an elution gradient 0 to 1% EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford (S)-methyl 4-((1-cyclohexylethyl)amino)-3- nitrobenzoate (7.00 g, 91 %) as a yellow oil which solidified on standing. 1 H NMR (400 MHz, DMSO-d 6 ): δ 8.63 (d, 1H), 8.35 (d, 1H), 7.96 (dd, 1H), 7.23 (d, 1H), 3.83 (s, 5H), 1.75 (m, 5H), 1.57 (m, 3H), 1.14 (m, 11H), 0.84 (m, 1H); HPLC-MS (m/z) [M+H]+ = ; HPLC t R = min. Excess H 2 was added slowly to a stirred solution of Pd/C (1.21 g, 11.4 mmol) and (S)-methyl 4-((1-cyclohexylethyl)amino)-3-nitrobenzoate (7.00 g, 22.8 mmol) in EtOAc/MeOH (40 ml of a 1:1 mixture). The resulting mixture was stirred at room temperature for 4 hours, and then filtered through a pad of diatomaceous earth. The solvent was removed under reduced pressure to afford (S)-methyl 3-amino-4-((1-cyclohexylethyl)amino)benzoate (6.10 g, 96 %) as a green solid. The product was used in the next step directly without further purification. 1 H NMR (400 MHz, DMSO-d 6 ) δ 7.18 (m, 2H), 6.42 (d, 1H), 4.85 (m, 1H), 4.79 (s, 2H), 4.04 (m, 1H), 3.72 (s, 3H), 3.38 (m, 1H), 2.00 (s, 1H), 1.82 (d, 1H), 1.72 (m, 3H), 1.62 (m, 1H), 1.46 (m, 1H), 1.13 (m, 9H); HPLC-MS (m/z) [M+H]+ = ; HPLC t R = min. Iodine (2.72 g, 10.7 mmol) was added to sodium hydroxide (2.14 g, 53.5 mmol), 6- bromobenzo[d][1,3]dioxole-5-carbaldehyde (1.22 g, 5.35 mmol) and methyl (S)-3-amino-4- ((1-cyclohexylethyl)amino)benzoate (1.48 g, 5.35 mmol) in acetonitrile (15 ml) under nitrogen. The resulting mixture was stirred at room temperature for 60 minutes. The reaction mixture was acidified with 2M HCl to ph~3. The reaction mixture was then concentrated and diluted with EtOAc (50 ml), and washed sequentially with water (25 ml x 3), and saturated brine (15 ml x 3). The organic layer was dried over Na 2 SO 4, filtered and evaporated to afford crude product. The crude product was purified by flash C18-flash chromatography, elution gradient 0 to 100% MeCN in water. Pure fractions were evaporated to dryness to afford (S)-2-(6-bromobenzo[d][1,3]dioxol-5-yl)-1-(1-cyclohexylethyl)-1Hbenzo[d]imidazole-5-carboxylic acid (1.90 g, 75 %) as a brown solid. 1 H NMR (300 MHz, DMSO-d 6 ): δ (s, 1H), 8.24 (m, 1H), 7.87 (d, 2H), 7.43 (d, 1H), 7.10 (s, 1H), 6.22 (m, 2H), 4.02 (q, 1H), 3.74 (ddd, 1H), 1.98 (s, 2H), 1.87 (d, 1H), 1.64 (dd, 4H), 1.48 (d, 2H), 1.17 (t, 2H), 0.99 (s, 2H), 0.85 (s, 2H), 0.56 (d, 1H); HPLC-MS (m/z) [M+H]+ = ; HPLC t R = min. To a stirred solution of (S)-2-(6-bromobenzo[d][1,3]dioxol-5-yl)-1-(1-cyclohexylethyl)-1Hbenzo[d]imidazole-5-carboxylic acid (0.080 g, 0.17 mmol) in DCM (2 ml) were added HATU (0.129 g, 0.34 mmol) and then 4-aminobenzonitrile (0.03 g, 0.25 mmol) and N-ethyl- N-isopropylpropan-2-amine (0.044 g, 0.34 mmol). The reaction mixture was stirred at room temperature for 16 hrs, and then heated at 40 C for 6 hrs. The DCM was removed by 3
4 RESEARCH SUPPLEMENTARY INFORMATION vacuum, then 1.5 ml of DMF was added. The reaction mixture was heated at 80 C for 3 hrs and then EtOAc was added (30 ml). This solution was washed with water (3 x 30 ml), brine (30 ml), dried over Na 2 SO 4, filtered and concentrated. The residue was purified with flash chromatography (SiO 2 ), hexanes/etoac) to give off-white solid. 1 H NMR (400 MHz, DMSO-d 6 ): δ (br. s., 1H), (m, 1H), (m, 2H), (m, 1H), (m, 3H), (m, 2H), (m, 1H), (m, 1H), (m, 1H), 1.69 (d, J = 7.0 Hz, 3H), (m, 1H), (m, 2H), (m, 1H), (m, 4H), (m, 1H); 13 C NMR (100 MHz, DMSO-d 6 ): δ 167.0, 154.5, 150.2, 147.6, 144.3, 135.5, 133.5, 128.6, 125.2, 122.9, 120.5, 120.0, 119.6, 115.1, 113.1, 112.8, 112.5, 105.5, 103.2, 58.8, 41.7, 30.3, 25.9, 25.8, 18.0, 17.7; UPLC-MS (m/z) [M+H]+ = 570.1; HPLC t R = 1.37 min. HRMS (m/z) [M+] calcd for C 30 H 28 BrN 4 O 3 ; , found ,3-Dihydro-1H,1'H-2,3'-biindole-1-carbaldehyde (AZ7188). 1H-Indole (5.00 g, 42.6 mmol) was added portionwise to HCl in toluene (107 ml, 213 mmol) in 0 C under nitrogen. The resulting mixture was stirred at 0 C for 3 hours. The reaction mixture was filtered through diatomaceous earth, and then diluted with DCM. The reaction mixture was adjusted to basic ph with saturated NaHCO 3. The organic layers were combined and washed with water (3 x 50 ml) to afford 3-(indolin-2-yl)-1H-indole (4.00g, 40% ) as a pink solid. 1 H NMR (300 MHz, DMSO-d 6 ): δ (m, 1H), (m, 1H), (m, 9H), (m, 1H), (m, 1H), (m, 1 H). HPLC-MS (m/z) [M+H]+ = 235.4; HPLC t R = min; EDC (2.97 g, 15.5 mmol) was added portionwise to formic acid (0.74 ml, 19.4 mmol) and 3- (indolin-2-yl)-1h-indole (2.27g, 9.69 mmol), Et 3 N (4.05 ml, mmol) in DCM (40 ml) at 0 C under nitrogen. The resulting mixture was stirred at 0 C for 4 hours. The reaction mixture was diluted with DCM. The organic layers were combined and washed with water (5 x 75 ml), and then the solvent was removed under reduced pressure. The crude product was purified by flash silica chromatography with an elution gradient 0 to 25 % EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford 2-(1H-indol-3- yl)indoline-1-carbaldehyde (1.10 g, 43.3 %) as a purple solid. Atropisomers observed in NMR spectra; 1 H NMR (500 MHz, DMSO-d 6, 27 C): δ (s, 1H), (s, 0H), 9.02 (d, J = 1.0 Hz, 0H), 8.31 (s, 1H), (m, 1H), 7.47 (d, J = 8.0 Hz, 0H), (m, 1H), (m, 2H), (m, 1H), 7.19 (d, J = 8.0 Hz, 0H), (m, 3H), 6.88 (dddd, J = 1.0, 7.0, 8.0, 12.0 Hz, 1H), 5.83 (td, J = 6.4, 10.1, 10.6 Hz, 1H), 3.69 (dd, J = 10.1, 16.5 Hz, 1H), 3.25 (dd, J = 5.5, 16.5 Hz, 1H), 3.07 (dd, J = 2.8, 16.4 Hz, 0H); 1 H NMR (500 MHz, DMSO-d 6, 100 C): δ (s, 1H), 8.54 (s, 1H), 7.84 (s, 1H), (m, 1H), (m, 1H), (m, 3H), (m, 2H), 6.91 (ddd, J = 1.0, 7.0, 8.0 Hz, 1H), 5.84 (dd, J = 4.7, 10.0 Hz, 1H), 3.70 (ddt, J = 1.1, 9.9, 16.3 Hz, 1H), (m, 1H); 13 C NMR (100 MHz, DMSO-d 6 ): δ 161.1, 158.9, 141.7, 141.6, 137.4, 137.1, 131.5, 131.3, 128.0, 127.8, 126.3, 125.5, 125.0, 124.8, 124.7, 124.4, 123.4, 122.0, 121.6, 119.5, 119.1, 118.9, 116.3, 115.6, 112.5, 112.1, 110.6, 56.2, 53.9, 36.4; HPLC-MS (m/z) [M+H]+ = 263.0; HPLC t R = min; HRMS (m/z) [M+] calcd for C 17 H 15 N 2 O; , found
5 RESEARCH Abbreviations DCM = dichloromethane DMF = dimethylformamide DMSO = dimethylsulfoxide EDC = 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide EtOAc = ethyl acetate Et 3 N = triethylamine HATU = (1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate) HPLC t R = retention time on high pressure liquid chromatography LC-MS = liquid chromatography mass spectrometry MeCN = acetonitrile MeOH = methanol TLC = thin layer chromatography UPLC-MS = ultra performance liquid chromatography mass spectrometry 5
SUPPLEMENTARY INFORMATION
doi:10.1038/nature24451 Chemical synthesis of USP7 compounds General 1 H, 13 C and 19 F nuclear magnetic resonance (NMR) spectra were obtained on either Bruker or Varian spectrometers at 300 or 400 MHz,
More informationSupporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials
Supporting Material 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Srinivas Olepu a, Praveen Kumar Suryadevara a, Kasey Rivas b, Christophe L. M. J. Verlinde
More informationSupporting Information
Supporting Information Total Synthesis of (±)-Grandilodine B Chunyu Wang, Zhonglei Wang, Xiaoni Xie, Xiaotong Yao, Guang Li, and Liansuo Zu* School of Pharmaceutical Sciences, Tsinghua University, Beijing,
More informationElectronic Supplementary Material (ESI) for Medicinal Chemistry Communications This journal is The Royal Society of Chemistry 2012
Supporting Information. Experimental Section: Summary scheme H 8 H H H 9 a H C 3 1 C 3 A H H b c C 3 2 3 C 3 H H d e C 3 4 5 C 3 H f g C 2 6 7 C 2 H a C 3 B H c C 3 General experimental details: All solvents
More informationTetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon
SUPPLEMENTARY METHODS Solvents, reagents and synthetic procedures All reactions were carried out under an argon atmosphere unless otherwise specified. Tetrahydrofuran (THF) was distilled from benzophenone
More informationAll solvents and reagents were used as obtained. 1H NMR spectra were recorded with a Varian
SUPPLEMETARY OTE Chemistry All solvents and reagents were used as obtained. 1H MR spectra were recorded with a Varian Inova 600 MR spectrometer and referenced to dimethylsulfoxide. Chemical shifts are
More informationAn Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol
An Efficient Total Synthesis and Absolute Configuration Determination of Varitriol Ryan T. Clemens and Michael P. Jennings * Department of Chemistry, University of Alabama, 500 Campus Dr. Tuscaloosa, AL
More informationSupporting Information. (1S,8aS)-octahydroindolizidin-1-ol.
SI-1 Supporting Information Non-Racemic Bicyclic Lactam Lactones Via Regio- and cis-diastereocontrolled C H insertion. Asymmetric Synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.
More informationSupporting Information for
Page of 0 0 0 0 Submitted to The Journal of Organic Chemistry S Supporting Information for Syntheses and Spectral Properties of Functionalized, Water-soluble BODIPY Derivatives Lingling Li, Junyan Han,
More informationSupporting Information
Supporting Information Organocatalytic Enantioselective Formal Synthesis of Bromopyrrole Alkaloids via Aza-Michael Addition Su-Jeong Lee, Seok-Ho Youn and Chang-Woo Cho* Department of Chemistry, Kyungpook
More informationSupporting Information. Identification and synthesis of impurities formed during sertindole
Supporting Information Identification and synthesis of impurities formed during sertindole preparation I. V. Sunil Kumar* 1, G. S. R. Anjaneyulu 1 and V. Hima Bindu 2 for Address: 1 Research and Development
More informationFast and Flexible Synthesis of Pantothenic Acid and CJ-15,801.
Fast and Flexible Synthesis of Pantothenic Acid and CJ-15,801. Alan L. Sewell a, Mathew V. J. Villa a, Mhairi Matheson a, William G. Whittingham b, Rodolfo Marquez a*. a) WestCHEM, School of Chemistry,
More informationSimplified platensimycin analogues as antibacterial agents
Simplified platensimycin analogues as antibacterial agents Dragan Krsta, a Caron Ka, a Ian T. Crosby, a Ben Capuano a and David T. Manallack a * a Medicinal Chemistry and Drug Action, Monash Institute
More informationThe First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C
Supporting Information The First Asymmetric Total Syntheses and Determination of Absolute Configurations of Xestodecalactones B and C Qiren Liang, Jiyong Zhang, Weiguo Quan, Yongquan Sun, Xuegong She*,,
More informationFormal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis
Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis Kazushi Watanabe, Yuto Suzuki, Kenta Aoki, Akira Sakakura, Kiyotake Suenaga, and Hideo Kigoshi* Department of Chemistry,
More informationSUPPLEMENTARY INFORMATION
Synthetic chemistry ML5 and ML4 were identified as K P.(TREK-) activators using a combination of fluorescence-based thallium flux and automated patch-clamp assays. ML5, ML4, and ML5a were synthesized using
More informationCoupling of 6 with 8a to give 4,6-Di-O-acetyl-2-amino-2-N,3-O-carbonyl-2-deoxy-α-Dglucopyranosyl-(1 3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose.
General Experimental Procedures. NMR experiments were conducted on a Varian Unity/Inova 400-MHz Fourier Transform NMR Spectrometer. Chemical shifts are downfield from tetramethylsilane in CDCl 3 unless
More informationSupporting Information
Supporting Information SmI 2 -Mediated Carbon-Carbon Bond Fragmentation in α-aminomethyl Malonates Qiongfeng Xu,, Bin Cheng, $, Xinshan Ye,*, and Hongbin Zhai*,,,$ The State Key Laboratory of Natural and
More informationSupporting Information
Supporting Information Synthesis of H-Indazoles from Imidates and Nitrosobenzenes via Synergistic Rhodium/Copper Catalysis Qiang Wang and Xingwei Li* Dalian Institute of Chemical Physics, Chinese Academy
More informationSynthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes
Supporting Information to Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes Yan Zhang*, Dongmei Guo, Shangyi
More informationhydroxyanthraquinones related to proisocrinins
Supporting Information for Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins Joyeeta Roy, Tanushree Mal, Supriti Jana and Dipakranjan Mal* Address: Department of Chemistry,
More informationSupplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4)
Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4) A solution of propenyl magnesium bromide in THF (17.5 mmol) under nitrogen atmosphere was cooled in an ice bath and
More informationSupporting Information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Supporting Information Content Synthesis of compounds 2a, 2b in Scheme
More informationDiscovery of 3-substituted 1H-indole-2-carboxylic Acid Derivatives as a Novel Class of CysLT 1 Selective Antagonists
Discovery of 3-substituted 1H-indole-2-carboxylic Acid Derivatives as a Novel Class of CysLT 1 Selective Antagonists Huayan Chen,,b Hui Yang, #, b Zhilong Wang, # Xin Xie, #, * Fajun Nan, * State Key Laboratory
More informationCompound Number. Synthetic Procedure
Compound Number 1 2 3 4 5 Synthetic Procedure Compound 1, KY1220, (Z)-5-((1-(4-nitrophenyl)-1H-pyrrol-2-yl)methylene)-2-thioxoimidazolidin-4-one was purchased from Chemdiv, Catalog #3229-2677, 97% HPLC
More informationOrganocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine
Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine Ying Xie, a Hongjie Pan, a Xiao Xiao, a Songlei Li a and Yian Shi* a,b a Beijing National Laboratory for
More informationOpioid ligands with mixed properties from substituted enantiomeric N-phenethyl-5-
Supplementary Information for: Opioid ligands with mixed properties from substituted enantiomeric N-phenethyl-5- phenylmorphans. Synthesis of a μ-agonist δ antagonist and δ-inverse agonists Kejun Cheng,
More informationSynthesis and Use of QCy7-derived Modular Probes for Detection and. Imaging of Biologically Relevant Analytes. Supplementary Methods
Synthesis and Use of QCy7-derived Modular Probes for Detection and Imaging of Biologically Relevant Analytes Supplementary Methods Orit Redy a, Einat Kisin-Finfer a, Shiran Ferber b Ronit Satchi-Fainaro
More informationSupporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A
Fuerst et al. Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A S1 Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers:
More informationMolecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe
Supporting Information for Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe Ho Yu Au-Yeung, Jefferson Chan, Teera Chantarojsiri and Christopher J. Chang* Departments
More informationSupplementary Figure 1. Primary protein sequence alignment of engineered AcEZH2_ X,
Supplementary Figure 1. Primary protein sequence alignment of engineered AcEZH2_ X, HsEZH2 (Q15910) and AcEZH2 (G1KPH4) 1. Sequence alignment was performed using BLAST. A c t i v i t y ( n o r m a l i
More informationSUPPLEMENTARY INFORMATION
Supplementary Method Synthesis of 2-alkyl-MPT(R) General information (R) enantiomer of 2-alkyl (18:1) MPT (hereafter designated as 2-alkyl- MPT(R)), was synthesized as previously described 1, with some
More informationSupporting Information
1 A regiodivergent synthesis of ring A C-prenyl flavones Alberto Minassi, Anna Giana, Abdellah Ech-Chahad and Giovanni Appendino* Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche
More informationSynthesis of borinic acids and borinate adducts using diisopropylaminoborane
Synthesis of borinic acids and borinate adducts using diisopropylaminoborane Ludovic Marciasini, Bastien Cacciuttolo, Michel Vaultier and Mathieu Pucheault* Institut des Sciences Moléculaires, UMR 5255,
More information1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in
Supplementary Figure 1. Optical properties of 1 in various solvents. UV/Vis (left axis) and fluorescence spectra (right axis, ex = 420 nm) of 1 in hexane (blue lines), toluene (green lines), THF (yellow
More informationSupporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2002
Supporting Information for Angew. Chem. Int. Ed. Z50016 Wiley-VCH 2002 69451 Weinheim, Germany Total Synthesis of (±)-Wortmannin Takashi Mizutani, Shinobu Honzawa, Shin-ya Tosaki, and Masakatsu Shibasaki*
More informationSupporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S
Supporting Text Synthesis of (2S,3S)-2,3-bis(3-bromophenoxy)butane (3). Under N 2 atmosphere and at room temperature, a mixture of 3-bromophenol (0.746 g, 4.3 mmol) and Cs 2 C 3 (2.81 g, 8.6 mmol) in DMS
More informationSupporting Information for: Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions
Supporting Information for: Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions Patrick S. Fier* and Kevin M. Maloney* S1 General experimental details All reactions
More informationSupplementary Information
Supplementary Information C aryl -C alkyl bond formation from Cu(ClO 4 ) 2 -mediated oxidative cross coupling reaction between arenes and alkyllithium reagents through structurally well-defined Ar-Cu(III)
More informationSolvent-Controlled Pd(II)-Catalyzed Aerobic Chemoselective. Intermolecular 1,2-Aminooxygenation and 1,2-Oxyamination of
Supporting Information Solvent-Controlled Pd(II)-Catalyzed Aerobic Chemoselective Intermolecular 1,2-Aminooxygenation and 1,2-Oxyamination of Conjugated Dienes for the Synthesis of Functionalized 1,4-Benzoxazines
More informationDivergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site of Acid Catalysts
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Divergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site
More informationguanidine bisurea bifunctional organocatalyst
Supporting Information for Asymmetric -amination of -keto esters using a guanidine bisurea bifunctional organocatalyst Minami Odagi* 1, Yoshiharu Yamamoto 1 and Kazuo Nagasawa* 1 Address: 1 Department
More informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supporting Information TEMPO-catalyzed Synthesis of 5-Substituted Isoxazoles from Propargylic
More informationHualong Ding, Songlin Bai, Ping Lu,* Yanguang Wang*
Supporting Information for Preparation of 2-Amino-3-arylindoles via Pd-Catalyzed Coupling between 3-Diazoindolin-2-imines and Arylboronic Acids as well as Their Extension to 3-Aryl-3-fluoroindolin-2-imines
More informationMetal-free general procedure for oxidation of secondary amines to nitrones
S1 Supporting information Metal-free general procedure for oxidation of secondary amines to nitrones Carolina Gella, Èric Ferrer, Ramon Alibés, Félix Busqué,* Pedro de March, Marta Figueredo,* and Josep
More informationGeneral Procedures. Nature Chemical Biology: doi: /nchembio.1735
General Procedures All commercial chemicals and solvents are reagent grade and were used without further purification unless otherwise specified. All reactions except those in aqueous media were carried
More informationSupporting Information
Supporting Information Wiley-VCH 2006 69451 Weinheim, Germany rganocatalytic Conjugate Addition of Malonates to a,ß-unsaturated Aldehydes: Asymmetric Formal Synthesis of (-)-Paroxetine, Chiral Lactams
More informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 214 Supporting Information Rapid and sensitive detection of acrylic acid using a novel fluorescence
More informationSupporting Information
Supporting Information Wiley-VCH 2012 69451 Weinheim, Germany Concise Syntheses of Insect Pheromones Using Z-Selective Cross Metathesis** Myles B. Herbert, Vanessa M. Marx, Richard L. Pederson, and Robert
More informationAziridine in Polymers: A Strategy to Functionalize Polymers by Ring- Opening Reaction of Aziridine
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information (ESI) Aziridine in Polymers: A Strategy to Functionalize
More informationEnantioselective Synthesis of Fused Heterocycles with Contiguous Stereogenic Centers by Chiral Phosphoric Acid-Catalyzed Symmetry Breaking
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Enantioselective Synthesis of Fused Heterocycles with Contiguous Stereogenic Centers by Chiral
More informationSupporting Information
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2012 Subcellular Localization and Activity of Gambogic Acid Gianni Guizzunti,* [b] Ayse Batova, [a] Oraphin Chantarasriwong,
More informationSupporting Information For:
Supporting Information For: Peptidic α-ketocarboxylic Acids and Sulfonamides as Inhibitors of Protein Tyrosine Phosphatases Yen Ting Chen, Jian Xie, and Christopher T. Seto* Department of Chemistry, Brown
More informationdichloropyrimidine (1.5 g, 10.1 mmol) in THF (10 ml) added at -116 C under nitrogen atmosphere.
Supporting Information Experimental The presence of atropisomerism arising from diastereoisomerism is indicated in the 13 C spectra of the relevant compounds with the second isomer being indicated with
More informationSupporting Information:
Enantioselective Synthesis of (-)-Codeine and (-)-Morphine Barry M. Trost* and Weiping Tang Department of Chemistry, Stanford University, Stanford, CA 94305-5080 1. Aldehyde 7. Supporting Information:
More informationSequential dynamic structuralisation by in situ production of
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Electronic Supplementary Information Sequential dynamic structuralisation by in situ production
More informationAminoacid Based Chiral N-Amidothioureas. Acetate Anion. Binding Induced Chirality Transfer
Aminoacid Based Chiral -Amidothioureas. Acetate Anion Binding Induced Chirality Transfer Fang Wang, a Wen-Bin He, a Jin-He Wang, a Xiao-Sheng Yan, a Ying Zhan, a Ying-Ying Ma, b Li-Cai Ye, a Rui Yang,
More informationSynthesis of Dihydroquinoline Based Merocyanines as Naked Eye and Fluorogenic sensors for Hydrazine Hydrate in Aqueous Medium
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Synthesis of Dihydroquinoline Based Merocyanines as Naked Eye and Fluorogenic sensors for Hydrazine
More informationEnantioselective Organocatalytic Michael Addition of Malonate Esters to Nitro Olefins Using Bifunctional Cinchonine Derivatives
Enantioselective rganocatalytic Michael Addition of Malonate Esters to itro lefins Using Bifunctional Cinchonine Derivatives Jinxing Ye, Darren J. Dixon * and Peter S. Hynes School of Chemistry, University
More informationDomino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes
Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Jian Gong, Fuchun Xie, Wenming Ren, Hong Chen and Youhong Hu* State Key Laboratory of Drug Research,
More informationSynthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity
Supporting Information for Synthesis of Glaucogenin D, a Structurally Unique Disecopregnane Steroid with Potential Antiviral Activity Jinghan Gui,* Hailong Tian, and Weisheng Tian* Key Laboratory of Synthetic
More informationSupporting Information
Supporting Information ACA: A Family of Fluorescent Probes that Bind and Stain Amyloid Plaques in Human Tissue Willy M. Chang, a Marianna Dakanali, a Christina C. Capule, a Christina J. Sigurdson, b Jerry
More informationBlock: Synthesis, Aggregation-Induced Emission, Two-Photon. Absorption, Light Refraction, and Explosive Detection
Electronic Supplementary Information (ESI) Luminogenic Materials Constructed from Tetraphenylethene Building Block: Synthesis, Aggregation-Induced Emission, Two-Photon Absorption, Light Refraction, and
More informationSupplementary Material. Ionic liquid iodinating reagent for mild and efficient iodination of. aromatic and heteroaromatic amines and terminal alkynes
Supplementary Material onic liquid iodinating reagent for mild and efficient iodination of aromatic and heteroaromatic amines and terminal alkynes Mahboobe Nouzarian 1, Rahman Hosseinzadeh 1,*, and Hamid
More informationSupporting Information
Supporting Information for Engineering of indole-based tethered biheterocyclic alkaloid meridianin into -carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization
More informationRing-Opening / Fragmentation of Dihydropyrones for the Synthesis of Homopropargyl Alcohols
Ring-pening / Fragmentation of Dihydropyrones for the Synthesis of Homopropargyl Alcohols Jumreang Tummatorn, and Gregory B. Dudley, * Department of Chemistry and Biochemistry, Florida State University,
More informationSupporting Information. Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones
Supporting Information Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones Marco Bandini,* Riccardo Sinisi, Achille Umani-Ronchi* Dipartimento di Chimica Organica G. Ciamician, Università
More informationSupporting Information. Table of Contents. 1. General Notes Experimental Details 3-12
Supporting Information Table of Contents page 1. General Notes 2 2. Experimental Details 3-12 3. NMR Support for Timing of Claisen/Diels-Alder/Claisen 13 4. 1 H and 13 C NMR 14-37 General Notes All reagents
More informationQile Wang, and Nan Zheng* Department of Chemistry and Biochemistry, University of Arkansas. Fayetteville, Arkansas,
Supporting Information A Photocatalyzed Synthesis of Naphthalenes by Using Aniline as a Traceless Directing Group in [4+2] Annulation of AminoBenzocyclobutenes with Alkynes Qile Wang, and Nan Zheng* Department
More informationKinetics experiments were carried out at ambient temperature (24 o -26 o C) on a 250 MHz Bruker
Experimental Materials and Methods. All 31 P NMR and 1 H NMR spectra were recorded on 250 MHz Bruker or DRX 500 MHz instruments. All 31 P NMR spectra were acquired using broadband gated decoupling. 31
More informationAccessory Information
Accessory Information Synthesis of 5-phenyl 2-Functionalized Pyrroles by amino Heck and tandem amino Heck Carbonylation reactions Shazia Zaman, *A,B Mitsuru Kitamura B, C and Andrew D. Abell A *A Department
More informationSupporting Information. A rapid and efficient synthetic route to terminal. arylacetylenes by tetrabutylammonium hydroxide- and
Supporting Information for A rapid and efficient synthetic route to terminal arylacetylenes by tetrabutylammonium hydroxide- and methanol-catalyzed cleavage of 4-aryl-2-methyl-3- butyn-2-ols Jie Li and
More informationSupporting Information
Supporting Information Synthesis of the natural product Marthiapeptide A Yuqi Zhang 1, Md. Amirul Islam 1 and Shelli R. McAlpine 1* 1 School of Chemistry, University of New South Wales, Sydney, NSW 2052
More informationSUPPORTING INFORMATION
UPPRTING INFRMATIN Application of a Rhodium-Catalyzed Addition/Cyclization equence Toward the ynthesis of Polycyclic eteroaromatics Nai-Wen Tseng and Mark Lautens* Davenport Laboratories, Chemistry Department,
More informationSupporting Information
Supporting Information Novel diphenylmethyl-derived amide protecting group for efficient liquid-phase peptide synthesis; AJIPHASE Daisuke Takahashi*, Tatsuya Yano and Tatsuya Fukui Research Institute For
More informationHalogen halogen interactions in diiodo-xylenes
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) for CrystEngComm. This journal is The Royal Society
More informationPhotooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins
S1 Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins Antonia Kouridaki, Tamsyn Montagnon, Maria Tofi and Georgios Vassilikogiannakis* Department of
More informationSupporting Information for: Synthesis of Chiral Tryptamines via a Regioselective Indole Alkylation
Supporting Information for: Synthesis of Chiral Tryptamines via a Regioselective Indole Alkylation Jens Wolfard, Jie Xu,* Haiming Zhang, and Cheol K. Chung* Department of Small Molecule Process Chemistry,
More informationSupporting Information. Application of the Curtius rearrangement to the synthesis of 1'- aminoferrocene-1-carboxylic acid derivatives
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018 Supporting Information Application
More informationSupplementary Information (Manuscript C005066K)
Supplementary Information (Manuscript C005066K) 1) Experimental procedures and spectroscopic data for compounds 6-12, 16-19 and 21-29 described in the paper are given in the supporting information. 2)
More informationMaksim A. Kolosov*, Olesia G. Kulyk, Elena G. Shvets, Valeriy D. Orlov
1 Synthesis of 5-cinnamoyl-3,4-dihydropyrimidine-2(1H)-ones Supplementary Information Maksim A. Kolosov*, lesia G. Kulyk, Elena G. Shvets, Valeriy D. rlov Department of organic chemistry, V.N.Karazin Kharkiv
More informationSupporting Information. Rh (III)-Catalyzed Meta-C H Olefination Directed by a Nitrile Template
Supporting Information Rh (III)-Catalyzed Meta-C H Olefination Directed by a Nitrile Template Hua-Jin Xu, Yi Lu, *, Marcus E. Farmer, Huai-Wei Wang, Dan Zhao, Yan-Shang Kang, Wei-Yin Sun, *, Jin-Quan Yu
More informationSupporting information. *Corresponding Author: Telephone number: , Fax number: ; address:
Supporting information Synthesis of indolizidine, pyrrolizidine and quinolizidine ring systems by proline-catalyzed sequential -amination and HWE olefination of an aldehyde Shruti Vandana Kauloorkar, a
More informationTotal Synthesis of (±)-Vibsanin E. Brett D. Schwartz, Justin R. Denton, Huw M. L. Davies and Craig. M. Williams. Supporting Information
Total Synthesis of (±)-Vibsanin E. Brett D. Schwartz, Justin R. Denton, Huw M. L. Davies and Craig M. Williams Supporting Information General Methods S-2 Experimental S-2 1 H and 13 C NMR Spectra S-7 Comparison:
More informationDiaza [1,4] Wittig-type rearrangement of N-allylic-N- Boc-hydrazines into -amino-n-boc-enamines
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Diaza [1,4] Wittig-type rearrangement of N-allylic-N- Boc-hydrazines into -amino-n-boc-enamines
More informationSupporting Information
Supporting Information Wiley-VCH 25 69451 Weinheim, Germany Direct Asymmetric α-fluorination of Aldehydes [**] Derek D. Steiner, Nobuyuki Mase, Carlos F. Barbas III* [*] Prof. Dr. C. F. Barbas III, Derek
More informationSupporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Pd-Catalyzed C-H Activation/xidative Cyclization of Acetanilide with orbornene:
More information(Supplementary Information)
Foldamer-mediated Structural Rearrangement Attenuates Aβ Oligomerization and Cytotoxicity (Supplementary Information) Sunil Kumar* 1, Anja Henning-Knechtel 2, Ibrahim Chehade 2, Mazin Magzoub 2, and Andrew
More informationpyrazoles/isoxazoles library using ketene dithioacetals
Water mediated construction of trisubstituted pyrazoles/isoxazoles library using ketene dithioacetals Mahesh M. Savant, Akshay M. Pansuriya, Chirag V. Bhuva, Naval Kapuriya, Anil S. Patel, Vipul B. Audichya,
More informationSupporting Information
Supporting Information Design and Enantioselective Synthesis of β-vinyl Tryptamine Building Blocks for Construction of Privileged Chiral Indole Scaffolds Tao-Yan Lin, Hai-Hong Wu, Jian-Jun Feng*, and Junliang
More informationElectronic supplementary information. Strong CIE activity, multi-stimuli-responsive fluorescence and data
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 2015 Electronic supplementary information Strong CIE activity, multi-stimuli-responsive
More informationSupporting Information
Supporting Information Total Synthesis and Structural Reassignment of (±)-Cereoanhydride Zhiqiang Ren, Yu Hao, Xiangdong Hu* Department of Chemistry & Material Science, Key Laboratory of Synthetic and
More informationSupporting Information
Supporting Information Divergent Reactivity of gem-difluoro-enolates towards Nitrogen Electrophiles: Unorthodox Nitroso Aldol Reaction for Rapid Synthesis of -Ketoamides Mallu Kesava Reddy, Isai Ramakrishna,
More informationThe Enantioselective Synthesis and Biological Evaluation of Chimeric Promysalin Analogs Facilitated by Diverted Total Synthesis
S1 The Enantioselective Synthesis and Biological Evaluation of Chimeric Promysalin Analogs Facilitated by Diverted Total Synthesis Kyle W. Knouse and William M. Wuest* Department of Chemistry, Temple University,
More informationRed Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via Chiral Transfer of the Conjugated
More informationSupplemental data. Supplemental Figure 1: Alignment of potential ERRE1 and 2 in human, mouse and rat. PEPCK promoter.
1 Supplemental data A Supplemental Figure 1: Alignment of potential ERRE1 and 2 in human, mouse and rat PEPCK promoter. 2 A B C Supplemental Figure 2: Molecular structures of 4-T analogs. a-b, GSK5182
More informationSupplemental material for: Concise Total Syntheses of (±)-Mesembrane and (±)-Crinane. Table of Contents
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Das, De, Shubhashish and Bisai Supporting Information 1 Supplemental material
More informationSupporting Information
Supporting Information Wiley-VCH 2006 69451 Weinheim, Germany A Highly Enantioselective Brønsted Acid Catalyst for the Strecker Reaction Magnus Rueping, * Erli Sugiono and Cengiz Azap General: Unless otherwise
More informationSYNTHESIS OF A 3-THIOMANNOSIDE
Supporting Information SYNTHESIS OF A 3-THIOMANNOSIDE María B Comba, Alejandra G Suárez, Ariel M Sarotti, María I Mangione* and Rolando A Spanevello and Enrique D V Giordano Instituto de Química Rosario,
More informationBrønsted Base-Catalyzed Reductive Cyclization of Alkynyl. α-iminoesters through Auto-Tandem Catalysis
Supporting Information Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl α-iminoesters through Auto-Tandem Catalysis Azusa Kondoh, b and Masahiro Terada* a a Department of Chemistry, Graduate School
More information