Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain
|
|
|
- Sharleen Bailey
- 5 years ago
- Views:
Transcription
1 rganic Lett. (Supporting Information) 1 Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain Charles Kim, Richard Hoang and Emmanuel A. Theodorakis* Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California Supporting Information General techniques. rganic solutions were concentrated by rotary evaporation below 45 C at about 20 mmhg. All nonaqueous reactions were carried out using flame-dried glassware, under an argon atmosphere in dry, freshly distilled solvents under anhydrous conditions, unless otherwise noted. THF and Et 2 were distilled from sodium/benzophenone; CH 2 Cl 2 and toluene from calcium hydride; and benzene from potassium. Pyridine, triethylamine and boron trifluoride etherate were distilled from calcium hydride prior to use. Yields refer to chromatographically and spectroscopically ( 1 H NMR) homogeneous materials, unless otherwise stated. Reactions were monitored by thin-layer chromatography carried out on 0.25 mm E. rck silica gel plates (60F-254) using UV light as visualizing agent and p-anisaldehyde solution and heat as developing agents. E. rck silica gel (60, particle size mm) was used for flash chromatography. Preparative thin-layer chromatography separations were carried out on 0.25 or 0.50 mm E. rck silica gel plates (60F-254). NMR spectra were recorded on a Varian 400 MHz instrument and calibrated using residual undeuterated solvent as an internal reference. IR spectra were recorded on a Perkin-Elmer Model 781 spectrometer. ptical rotations were recorded on a Perkin-Elmer 241 polarimeter. High resolution mass
2 16 16 Cl H rganic Lett. (Supporting Information) 2 spectra (HRMS) were recorded on a VG 7070 HS mass spectrometer under chemical ionization (CI) conditions or on a VG ZAB-ZSE mass spectrometer under fast atom bombardment (FAB) conditions. lting points (mp) are uncorrected, and were recorded on a Thomas Hoover Unimelt capillary melting point apparatus. Procedures 9 To a suspension of D-mannose (8) (50 g, 0.28 mol) in 2.5 L of acetone was added iodine (14.21 g, mol) and the mixture was stirred for 2 h at 25 C. The reaction mixture was quenched at 0 C with sodium thiosulfate and sodium bicarbonate and the organic residues extracted with chloroform. After three washings with sodium bicarbonate (ca. 300 ml), the organic layer was dried over MgS4, concentrated and crystallized from an acetone/hexane mixture to produce 9 (60 g, 0.24 mol, 85%). 9: colorless solid; Rf = 0.33 (silica, 50% ether in hexanes); 1 H NMR (400 MHz, CDCl 3 ) d 5.38 (1H, d, J= 2.4Hz), 4.81 (1H, dd, J= 3.6, 6 Hz), 4.62 (1H, d, J= 6.0 Hz), 4.40 (1H, m), 4.18 (1H, dd, J= 3.6, 7.2 Hz), 4.06 (2H, m), 2.57 (1H, bs), 1.46 (3H, s), 1.45 (3H, s), 1.38 (3H, s), 1.32 (3H, s); 13 C NMR (100 MHz, CDCl 3 ) d 112.4, 108.9, 100.9, 85.3, 79.9, 79.5, 73.2, 66.3, 26.7, 25.8, 25.1, A solution of compound 9 (20 g, mol) in dry methylene chloride was treated sequentially with DMAP (5.64 g, mol), tosyl chloride (16.32 g, mol) and triethylamine (10.7 ml, mol). The reaction mixture was stirred at 25 C until TLC showed completion of reaction (approx. 2 h) at which time the solution was washed with aqueous copper sulfate, sodium bicarbonate and extracted with ethyl ether. The organic layer was extracted with sodium chloride (3 X 200 ml), dried over MgS4, concentrated and chromatographed (silica, 10-50% ether in
3 7 Bn 1611 rganic Lett. (Supporting Information) 3 hexanes) to afford 10 (13.5 g, 46.2 mmol, 60%). 10: viscous, amber-colored oil; Rf = 0.80 (50% ether in hexanes); 1 H NMR (400 MHz, CDCl 3 ) d 6.07 (1H, s), 4.96 (1H, d, J= 5.6Hz), 4.89 (1H, m), 4.44 (1H, m), 4.21 (1H, dd, J= 3.6, 11.2 Hz), 4.10 (1H, dd, J= 6.0, 8.8 Hz), 4.02 (1H, dd, J= 4.4, 8.8 Hz), 1.47 (3H, s), 1.46 (3H, s), 1.39 (3H, s), 1.33 (3H, s); 13 C NMR (100 MHz, CDCl 3 ) d 113.2, 109.4, 97.5, 89.1, 82.3, 78.5, 72.3, 66.7, 27.0, 25.9, 25.2, A solution of glycal 11 (2.0 g, 10 mmol) in THF (5 ml) at 0 C was treated under argon with sodium hydride (283 mg, 12 mmol), benzyl bromide (2.02 g, 12 mmol), and tetrabutyl ammonium iodide (0.198 g, 0.54 mmol). The reaction mixture was allowed to warm up to 25 C and stirred for 2 h at which time the TLC showed disappearance of the starting material. The reaction was quenched with brine and extracted with ether. The organic layer was washed with brine (3 X 50 ml), dried over MgS4, and concentrated. The residue was purified by flash chromatography (silica gel, 5-30% ether in hexanes) to produce compound 7 (2.5 g, 9 mmol, 90%). 7: viscous, bright-yellow oil; [a] 25 D: (c=1.0, CH 2 Cl 2 ); R f = 0.65 (30% ether in hexanes); IR (film) n max 2978, 2925, 1606, 1064; 1 H NMR (400 MHz, CDCl 3 ) d 7.32 (m, 5H), 6.62 (1H, d, J= 2.4 Hz), 5.29 (1H, t, J= 2.8 Hz), 4.66 (1H, m), 4.55 (3H, m), 4.44 (1H, dd, J= 4.4, 5.2 Hz), 4.12 (1H, m), 3.99 (1H, m), 1.47 (3H, s), 1.40 (3H, s); 13 C NMR (100 MHz, CDCl 3 ) d 150.3, 138.2, 128.1, 127.4, 127.3, 108.5, 101.7, 83.9, 79.1, 73.0, 70.9, 65.9, 26.6, H Bn H Et 6 Benzyl ether 7 (7.75 g, mol) was dissolved in CH 2 Cl 2 (30 ml) and a catalytic amount of rhodium acetate (0.023 g, 0.01 equiv.) was added to give a blue-green colored solution. As the solution
4 Bn H 5 rganic Lett. (Supporting Information) 4 was being stirred, ethyl diazoacetate (3.52 g, mol), dissolved in 40 ml of CH 2 Cl 2 was added via syringe pump over a period of 14 h. The reaction was carried out at 25 C and open to the atmosphere. After the completion of addition, the mixture was allowed to stir for another 3 h and then concentrated to reveal a blue, viscous oil. After silica gel separation the two isomeric cyclopropyl esters (4:1 ratio at the C13 center) were isolated together and were taken forward to the remaining steps. 6 (3.7 g, mmol, 45%). 6: (major isomer): R f = 0.75 (50% ether in hexanes); [a] 25 D : (c= 0.93, CH 2 Cl 2 ); IR (film) n max 2984, 2935, 1715, 1268, 1187, 1097; 1 H NMR (400 MHz, CDCl 3 ) d 7.35 (5H, m), 4.71 (1H, d, J= 11.6 Hz), 4.59 (1H, d, J= 12 Hz), 4.35 (2H, m), 4.18 (1H, d, J= 4.8 Hz), 4.07 (3H, m), 3.95 (1H, dd, J= 6.0, 8.4 Hz), 3.68 (1H, m), 2.34 (1H, t, J= 4.4, 4.8 Hz), 1.89 (1H, d, J= 2.8 Hz) 1.40 (3H, s), 1.36 (3H, s), 1.24 (3H, t, J= 6.8, 7.6 Hz); 13 C NMR (100 MHz, CDCl 3 ) d 170.6, 137.5, 128.2, 127.6, 127.5, 108.6, 81.9, 78.8, 72.7, 72.1, 66.5, 64.9, 60.7, 28.5, 26.7, 25.4, 21.4, 14.3; HRMS, calcd for C 20 H 26 6 (M+Na + ): , found: H A solution of ester 14 (0.929 g, 2.64 mmol) in dry CH 2 Cl 2 (90 ml) was cooled to -20 C and treated under argon with methanesulfonic acid (1 ml, 6 equiv) added dropwise via syringe. The temperature of the reaction mixture was allowed to rise to -5 C where it was stirred for 6 h. During this time the reaction mixture changed from a light yellow to a dark brown color. At the end of 6 h, the dry-ice bath was exchanged for an ice-water bath and allowed to stir for another 6 h. Upon completion of the reaction (TLC test, the cyclized product is distinctly more polar than the starting material) the reaction was quenched with a mixture of triethylamine and sodium bicarbonate and extracted with ethyl ether. The organic layer was washed with sodium bicarbonate (3 X 50 ml), dried over MgS 4 and concentrated. The resulting crude solid was chromatographed (silica, 30-80% ether in hexanes) to afford lactone 5 (0.491 g, 1.76
5 Bn H H 4 rganic Lett. (Supporting Information) 5 mmol, 67%). 5: yellowish solid; R f = 0.40 (80% ether in hexanes); [a] 25 D : (c= 0.85, CH 2 Cl 2 ); IR (film) n max 3634, 3528, 2918, 2861, 1780, 1731; 1 H NMR (400 MHz, CDCl 3 ) d 7.34 (3H, t, J= 7.2, 10 Hz), 7.23 (2H, d, J= 6.4 Hz), 6.33 (1H, d, J= 5.6 Hz), 4.54 (2H, m), 4.46 (1H, d, J= 11.6 Hz), 4.15 (1H, d, J= 4 Hz), 3.23 (1H, q, J= 5.6, 6.0 Hz), 2.84 (1H, dd, J= 19.2, 11.6 Hz), 2.33 (1H, dd, J= 5.2, 18.8 Hz), 2.27 (3H, s); 13 C NMR (100 MHz, CDCl 3 ) d 204.8, 173.5, 136.2, 128.5, 128.2, 127.6, 107.4, 85.4, 85.1, 72.2, 44.3, 31.1, 28.4; HRMS, calcd for C 15 H 16 5 (M+Cs + ): , found: A suspension of Urea-hydrogen peroxide (0.447 g, 4.75 mmol) in dry CH 2 Cl 2 (20 ml) was cooled to 0 C and treated with trifluoroacetic anhydride (0.336 ml, 2.38 mmol) added dropwise over a 5 minute period. The reaction mixture was brought up to 25 C and allowed to stir for 30 min and added via cannula to a solution of ketone 5 (0.164 g, mmol) in dry CH 2 Cl 2 (5 ml). After stirring at 25 C for 2h (completion by TLC), the reaction was quenched with sodium thiosulfate and sodium bicarbonate at 0 C and stirred for 0.5 h. The organic layer was diluted with ether and washed with sodium bicarbonate (3 X 20 ml). The organic layer was collected, dried over MgS 4, concentrated and purified (silica, 20-60% ether in hexanes) to afford compound 4 (0.12g, 69% yield). 4: white powdery solid; Rf = 0.30 (70% ether in hexanes); [a] 25 D : (c= 0.7, CH 2 Cl 2 ); IR (film) n max 2919, 2854, 1788, 1745, 1374, 1235, 1138; 1 H NMR (400 MHz, CDCl 3 ) d 7.35 (3H, t, J= 7.2, 9.2 Hz), 7.30 (2H, d, J= 7.6 Hz), 6.45 (1H, d, J= 4.0 Hz), 6.04 (1H, d, J= 6.0 Hz), 4.63 (1H, d, J= 11.6 Hz), (1H, d, J= 11.6 Hz), 3.88 (1H, qr, J= 4 Hz), 3.10 (1H, m), 2.79 (1H, dd, J= 9.2, 18.8 Hz), 2.48 (1H, dd, =2, J= 1.6, 18.8 Hz), 2.12 (3H, s); 13 C NMR (100 MHz, CDCl 3 ) d 172.7, 169.2, 136.5, 128.6, 128.4, 127.8, 105.3, 95.1, 81.9, 73.5, 41.7, 33.2, 21.1; HRMS, calcd for C 15 H 16 6 (M+Na + ): , found:
6 rganic Lett. (Supporting Information) 6 H 1 H 6 Bn H 5 H 2 H 3 H 4 CSY for compound 4: (H 1, H 2 ), (H 2, H 3, H 4, H 5 ), (H 5, H 6 ) H 1 H 6 Bn H 5 H 2 H 3 H 4 1D NE for compound 4: (H 4, H 5 )
7 rganic Lett. (Supporting Information) 7
8 rganic Lett. (Supporting Information) 8
9 rganic Lett. (Supporting Information) 9
10 rganic Lett. (Supporting Information) 10
11 rganic Lett. (Supporting Information) 11
12 rganic Lett. (Supporting Information) 12
13 rganic Lett. (Supporting Information) 13
14 rganic Lett. (Supporting Information) 14
15 rganic Lett. (Supporting Information) 15
16 rganic Lett. (Supporting Information) 16
17 rganic Lett. (Supporting Information) 17
18 rganic Lett. (Supporting Information) 18
19 rganic Lett. (Supporting Information) 19
20 rganic Lett. (Supporting Information) 20
21 rganic Lett. (Supporting Information) 21
Stereoselective Synthesis of (-) Acanthoic Acid
1 Stereoselective Synthesis of (-) Acanthoic Acid Taotao Ling, Bryan A. Kramer, Michael A. Palladino, and Emmanuel A. Theodorakis* Department of Chemistry and Biochemistry, University of California, San
Supporting 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
The 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*,,
Supporting 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,
Supporting 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
Supporting 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:
Regioselective Synthesis of the Tricyclic Core of Lateriflorone
Regioselective Synthesis of the Tricyclic Core of Lateriflorone Eric J. Tisdale, Hongmei Li, Binh G. Vong, Sun Hee Kim, Emmanuel A. Theodorakis* Department of Chemistry and Biochemistry, University of
Phil S. Baran*, Jeremy M. Richter and David W. Lin SUPPORTING INFORMATION
Direct Coupling of Pyrroles with Carbonyl Compounds: Short, Enantioselective Synthesis of (S)-Ketorolac Phil S. Baran*, Jeremy M. Richter and David W. Lin SUPPRTIG IFRMATI General Procedures. All reactions
Supporting 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.
A Strategy Toward the Synthesis of C 13 -Oxidized Cembrenolides
A Strategy Toward the Synthesis of C 13 -xidized Cembrenolides Alec Saitman, Steven D. E. Sullivan and Emmanuel A. Theodorakis* Department of Chemistry and Biochemistry, University of California, San Diego,
An 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
Supporting 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,
Synthesis 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
Supporting 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:
Tetrahydrofuran (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
Department of Chemistry and Biochemistry, California State University Northridge, Northridge, CA Experimental Procedures
Supporting Information Low Temperature n-butyllithium-induced [3,3]-Sigmatropic Rearrangement/Electrophile Trapping Reactions of Allyl-1,1- Dichlorovinyl Ethers. Synthesis of - - and -lactones. Aaron Christopher
Supplementary Material for: Unexpected Decarbonylation during an Acid- Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol.
Tetrahedron Letters 1 Pergamon TETRAHEDRN LETTERS Supplementary Material for: Unexpected Decarbonylation during an Acid- Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol. Jennifer L. Stockdill,
SYNTHESIS 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,
Supporting 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
Supplementary 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
An unusual dianion equivalent from acylsilanes for the synthesis of substituted β-keto esters
S1 An unusual dianion equivalent from acylsilanes for the synthesis of substituted β-keto esters Chris V. Galliford and Karl A. Scheidt* Department of Chemistry, Northwestern University, 2145 Sheridan
Supporting 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
Synthesis 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,
Supporting Information
Supporting Information Lewis acid-catalyzed intramolecular condensation of ynol ether-acetals. Synthesis of alkoxycycloalkene carboxylates Vincent Tran and Thomas G. Minehan * Department of Chemistry and
Supporting Information for. A New Method for the Cleavage of Nitrobenzyl Amides and Ethers
SI- 1 Supporting Information for A ew Method for the Cleavage of itrobenzyl Amides and Ethers Seo-Jung Han, Gabriel Fernando de Melo, and Brian M. Stoltz* The Warren and Katharine Schlinger Laboratory
Synthesis of fluorophosphonylated acyclic nucleotide analogues via Copper (I)- catalyzed Huisgen 1-3 dipolar cycloaddition
Synthesis of fluorophosphonylated acyclic nucleotide analogues via Copper (I)- catalyzed Huisgen 1-3 dipolar cycloaddition Sonia Amel Diab, Antje Hienzch, Cyril Lebargy, Stéphante Guillarme, Emmanuel fund
Formal 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,
Qile 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
Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol
S1 Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2010 Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol Julien
Total 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:
Supporting 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
Supplementary Material
10.1071/CH13324_AC CSIRO 2013 Australian Journal of Chemistry 2013, 66(12), 1570-1575 Supplementary Material A Mild and Convenient Synthesis of 1,2,3-Triiodoarenes via Consecutive Iodination/Diazotization/Iodination
Supporting Information
Supporting Information Wiley-VC 2008 69451 Weinheim, Germany SI-1 A Concise Approach to Vinigrol Thomas J. Maimone, Ana-Florina Voica, and Phil S. Baran* Contribution from the Department of Chemistry,
Supporting Information
Meyer, Ferreira, and Stoltz: Diazoacetoacetic acid Supporting Information S1 2-Diazoacetoacetic Acid, an Efficient and Convenient Reagent for the Synthesis of Substituted -Diazo- -ketoesters Michael E.
Supporting 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
Supporting 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
Highly stereocontrolled synthesis of trans-enediynes via
Supporting Information for Highly stereocontrolled synthesis of trans-enediynes via carbocupration of fluoroalkylated diynes Tsutomu Konno*, Misato Kishi, and Takashi Ishihara Address: Department of Chemistry
A Mild, Catalytic and Highly Selective Method for the Oxidation of α,β- Enones to 1,4-Enediones. Jin-Quan Yu, a and E. J.
A Mild, Catalytic and Highly Selective Method for the Oxidation of α,β- Enones to 1,4-Enediones Jin-Quan Yu, a and E. J. Corey b * a Department of Chemistry, Cambridge University, Cambridge CB2 1EW, United
Supporting 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
Indium Triflate-Assisted Nucleophilic Aromatic Substitution Reactions of. Nitrosobezene-Derived Cycloadducts with Alcohols
Supporting Information Indium Triflate-Assisted ucleophilic Aromatic Substitution Reactions of itrosobezene-derived Cycloadducts with Alcohols Baiyuan Yang and Marvin J. Miller* Department of Chemistry
Phil S. Baran*, Ryan A. Shenvi, Christos Mitsos SUPPORTING INFORMATION
A Remarkable Ring Contraction En Route to the Chartelline Alkaloids Phil S. Baran*, Ryan A. Shenvi, Christos Mitsos Contribution from the Department of Chemistry, The Scripps Research Institute, 10550
Synthesis 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
Photooxidations 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
N-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides
![N-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides](/thumbs/85/92425281.jpg "N-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides")
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Electronic supplementary information for -Hydroxyphthalimide: a new photoredox catalyst for [4+1]
Supporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Rh 2 (Ac) 4 -Catalyzed 2,3-Migration of -rrocenecarboxyl -Diazocarbonyl
Supporting Information
Supporting Information A Combined Effect of the Picoloyl Protecting Group and Triflic Acid in Sialylation Samira Escopy, Scott A. Geringer and Cristina De Meo * Department of Chemistry Southern Illinois
hydroxyanthraquinones 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,
Supporting Information for
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 2017 Supporting Information for
Electronic 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
Kinetics 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
Bulletin of the Chemical Society of Japan
Supporting Information Bulletin of the Chemical Society of Japan Enantioselective Copper-Catalyzed 1,4-Addition of Dialkylzincs to Enones Followed by Trapping with Allyl Iodide Derivatives Kenjiro Kawamura,
Accessory 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
Supporting Information
Supporting Information Precision Synthesis of Poly(-hexylpyrrole) and its Diblock Copolymer with Poly(p-phenylene) via Catalyst-Transfer Polycondensation Akihiro Yokoyama, Akira Kato, Ryo Miyakoshi, and
Fast 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,
Scalable Synthesis of Fmoc-Protected GalNAc-Threonine Amino Acid and T N Antigen via Nickel Catalysis
Scalable Synthesis of Fmoc-Protected GalNAc-Threonine Amino Acid and T N Antigen via Nickel Catalysis Fei Yu, Matthew S. McConnell, and Hien M. Nguyen* Department of Chemistry, University of Iowa, Iowa
SUPPORTING INFORMATION
SUPPRTING INFRMATIN A Direct, ne-step Synthesis of Condensed Heterocycles: A Palladium-Catalyzed Coupling Approach Farnaz Jafarpour and Mark Lautens* Davenport Chemical Research Laboratories, Chemistry
SUPPLEMENTARY 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
Experimental details
Supporting Information for A scalable synthesis of the (S)-4-(tert-butyl)-2-(pyridin-2-yl)-4,5-dihydrooxazole ((S)-t-BuPyx) ligand Hideki Shimizu 1,2, Jeffrey C. Holder 1 and Brian M. Stoltz* 1 Address:
Supporting 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
Ring-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,
Facile Synthesis of Flavonoid 7-O-Glycosides
Facile Synthesis of Flavonoid 7-O-Glycosides Ming Li, a Xiuwen Han, a Biao Yu b * a State Key Laboratory of Catalyst, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
Supplementary 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)
Supplemental 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
Supplementary 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)
A Sumanene-based Aryne, Sumanyne
A Sumanene-based Aryne, Sumanyne Niti Ngamsomprasert, Yumi Yakiyama, and Hidehiro Sakurai* Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871
Supporting Information: Regioselective esterification of vicinal diols on monosaccharide derivatives via
Supporting Information: Regioselective esterification of vicinal diols on monosaccharide derivatives via Mitsunobu reactions. Guijun Wang,*Jean Rene Ella-Menye, Michael St. Martin, Hao Yang, Kristopher
Supporting Information
Supporting Information (Tetrahedron. Lett.) Cavitands with Inwardly and Outwardly Directed Functional Groups Mao Kanaura a, Kouhei Ito a, Michael P. Schramm b, Dariush Ajami c, and Tetsuo Iwasawa a * a
Copper-Catalyzed Oxidative Cyclization of Carboxylic Acids
Copper-Catalyzed xidative Cyclization of Carboxylic Acids Supplementary material (51 pages) Shyam Sathyamoorthi and J. Du Bois * Department of Chemistry Stanford University Stanford, CA 94305-5080 General.
Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003
Supporting Information for Angew. Chem. Int. Ed. Z53001 Wiley-VCH 2003 69451 Weinheim, Germany 1 Ordered Self-Assembly and Electronic Behavior of C 60 -Anthrylphenylacetylene Hybrid ** Seok Ho Kang 1,
Synthesis of Cyclic Thioethers through Tandem C(sp 3 )- S and C(sp 2 )-S Bond Formations from α,β -Dichloro Vinyl Ketones
ynthesis of Cyclic Thioethers through Tandem C(sp 3 )- and C(sp 2 )- Bond Formations from α,β -Dichloro Vinyl Ketones Kyungsoo h,* Hyunjung Kim, Francesco Cardelli, Tamayi Bwititi, and Anna M. Martynow
A Total Synthesis of Paeoveitol
A Total Synthesis of Paeoveitol Lun Xu, Fengyi Liu, Li-Wen Xu, Ziwei Gao, Yu-Ming Zhao* Key Laboratory of Applied Surface and Colloid Chemistry of MOE & School of Chemistry and Chemical Engineering, Shaanxi
J. Am. Chem. Soc. Supporting Information Page 1
J. Am. Chem. Soc. Supporting Information Page 1 Short Total Synthesis of (±)-Sceptrin Phil S. Baran*, Alexandros L. Zografos, and Daniel P. Malley Contribution from the Department of Chemistry, The Scripps
Supporting 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
Total Synthesis of (±)-Gracilioether F
Total Synthesis of (±)-Gracilioether F Xin-Yue Shen, Xiao-Shui Peng,, Henry N. C. Wong*, Department of Chemistry, and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin,
Halogen 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
Supporting Information
Supporting Information Efficient Short Step Synthesis of Corey s Tamiflu Intermediate Nsiama Tienabe Kipassa, Hiroaki kamura, * Kengo Kina, Tetsuo Iwagawa, and Toshiyuki Hamada Department of Chemistry
Domino 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,
Chia-Shing Wu, Huai-An Lu, Chiao-Pei Chen, Tzung-Fang Guo and Yun Chen*
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Supporting Information Water/alcohol soluble electron injection material containing azacrown ether groups: Synthesis, characterization
Reactions. James C. Anderson,* Rachel H. Munday. School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK
Vinyl-dimethylphenylsilanes as Safety Catch Silanols in Fluoride free Palladium Catalysed Cross Coupling Reactions. James C. Anderson,* Rachel H. Munday School of Chemistry, University of Nottingham, Nottingham,
Supporting Information
An Improved ynthesis of the Pyridine-Thiazole Cores of Thiopeptide Antibiotics Virender. Aulakh, Marco A. Ciufolini* Department of Chemistry, University of British Columbia 2036 Main Mall, Vancouver, BC
Supporting 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
SUPPORTING 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,
Supporting Information for: Phosphonates
Supporting Information for: A Room-Temperature Alternative to the Arbuzov Reaction: the Reductive Deoxygenation of Acyl Phosphonates Sean M. A. Kedrowski and Dennis A. Dougherty* Division of Chemistry
A thermally-stable enzyme detection assay that amplifies signal autonomously in water without assistance from biological reagents
A thermally-stable enzyme detection assay that amplifies signal autonomously in water without assistance from biological reagents Table of Contents Kimy Yeung, Kyle M. Schmid, and Scott T. Phillips* Department
Coupling 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
Red 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
A Meldrum s Acid-Derived Thione Dienophile in a Convergent and Stereoselective Synthesis of a Tetracyclic Quassinoid Intermediate
A ldrum s Acid-Derived Thione Dienophile in a Convergent and Stereoselective Synthesis of a Tetracyclic Quassinoid Intermediate Stéphane Perreault and Claude Spino* Supporting Information Experimental
Supporting Information. Expeditious Construction of the DEF Ring System of Thiersinine B
Supporting Information Expeditious Construction of the DEF Ring System of Thiersinine B Masaru Enomoto and Shigefumi Kuwahara* Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural
Efficient Mono- and Bis-Functionalization of 3,6-Dichloropyridazine using (tmp) 2 Zn 2MgCl 2 2LiCl ** Stefan H. Wunderlich and Paul Knochel*
Efficient Mono- and Bis-Functionalization of 3,6-Dichloropyridazine using (tmp) 2 Zn 2Mg 2 2Li ** Stefan H. Wunderlich and Paul Knochel* Ludwig Maximilians-Universität München, Department Chemie & Biochemie
Supporting Information
Supporting Information Wiley-VCH 2012 69451 Weinheim, Germany Substitution of Two Fluorine Atoms in a Trifluoromethyl Group: Regioselective Synthesis of 3-Fluoropyrazoles** Kohei Fuchibe, Masaki Takahashi,
Brønsted 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
Effect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information (ESI) for Effect of Conjugation and Aromaticity of 3,6 Di-substituted
Supporting 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
Supporting Information for Sonogashira Hagihara reactions of halogenated glycals. Experimental procedures, analytical data and NMR spectra
Supporting Information for Sonogashira Hagihara reactions of halogenated glycals Dennis C. Koester and Daniel B. Werz* Address: Institut für Organische und Biomolekulare Chemie, Georg-August-Universität
SUPPORTING INFORMATION
SUPPORTING INFORMATION Synthesis of Functionalized Thia Analogues of Phlorins and Covalently Linked Phlorin-Porphyrin Dyads Iti Gupta a, Roland Fröhlich b and Mangalampalli Ravikanth *a a Department of
dichloropyrimidine (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
Supplementary Table S1: Response evaluation of FDA- approved drugs
SUPPLEMENTARY DATA, FIGURES AND TABLE BIOLOGICAL DATA Spheroids MARY-X size distribution, morphology and drug screening data Supplementary Figure S1: Spheroids MARY-X size distribution. Spheroid size was
Efficient Synthesis of Macrocyclic Ketones Via Palladium-Catalyzed Activation of Carboxylic Acids
ELECTRONIC SUPPORTING INFORMATION Efficient Synthesis of Macrocyclic Ketones Via Palladium-Catalyzed Activation of Carboxylic Acids Anant R. Kapdi, a,b * and Ian J. S. Fairlamb a, * a Department of Chemistry,
Drastically Decreased Reactivity of Thiols and Disulfides Complexed by Cucurbit[6]uril
![Drastically Decreased Reactivity of Thiols and Disulfides Complexed by Cucurbit[6]uril](/thumbs/94/119194061.jpg "Drastically Decreased Reactivity of Thiols and Disulfides Complexed by Cucurbit[6]uril")
SUPPORTING INFORMATION Drastically Decreased Reactivity of Thiols and Disulfides Complexed by Cucurbit[6]uril Lidia Strimbu Berbeci, Wei Wang and Angel E. Kaifer* Center for Supramolecular Science and
Synthesis 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