- Diastereoselective scalable synthesis of 2,6-trans-Piperidines using an aza-Michael reaction
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Highly efficient substrate and reagent controlled stereoselective synthesis of 2,6-trans-piperidine derivative (1) using an aza-Michael reaction is reported. This method was utilized to synthesize a variety of trans-piperidines on hundred-gram scales.
- Chowdhury, Somenath,Mao, Jianmin,Martynow, Jacek,Zhao, He,Duffy, Erin,Wu, Yusheng,Thakur, Vinay,Sirasani, Gopal,Tang, Yuanqing,Collin, Florine,Sinishtaj, Sandra,Bhattacharjee, Ashoke
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Read Online
- SIMPLE, STEREOSPECIFIC PREPARATION OF Z-3-IODOACRYLIC ACID FROM PROPIOLIC ACID AND METHYLMAGNESIUM IODIDE
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Addition of propiolic acid to 2.2 equiv of methylmagnesium iodide in THF followed by workup with acetic acid produces only the Z-isomer of 3-iodoacrylic acid, 2, in high yield.
- Jung, Michael E.,Hagenah, Jeffrey A.,Long-Mei, Zeng
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Read Online
- Revisiting the hydroiodination of propiolic acid
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Z-3-iodoacrylic acid Z-1, that formed by reacting propiolic acid 2 with 57% aqueous III at 80-85 °C, was efficiently converted into the isomeric acid E-1 by treatment in the same conditions.
- Zoller,Uguen
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Read Online
- Selective Ni-catalyzed cross-electrophile coupling of alkynes, fluoroalkyl halides, and vinyl halides
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We report a Ni-catalyzed three-component cross-electrophile coupling of alkynes with alkenyl halides and fluoroalkyl halides to generate fluoroalkyl-incorporated 1,3-dienes. This mild and operationally simple protocol is distinguished by its broad substra
- Chu, Lingling,Dai, Yubei,Wang, Fang,Zhu, Shengqing
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supporting information
(2022/01/26)
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- PYRROLO[2,3-D]PYRIMIDIN-2-ONE ANTIMICROBIAL COMPOUNDS
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The present disclosure relates generally to the field of antimicrobial compounds and to methods of making and using them. In some embodiments, the present disclosure provides pyrrolo[2,3-d]pyrimidin-2-ones useful for treating, preventing, reducing the risk of, and delaying the onset of microbial infections in humans and animals.
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(2020/07/05)
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- AMINOMETHYLAMIDINE AND METHYLAMIDINE ANTIMICROBIAL COMPOUNDS
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The present disclosure relates generally to the field of antimicrobial compounds and to methods of making and using them. In some embodiments, the present disclosure provides pyrrolo[2,3-d]pyrimidin-2-ones useful for treating, preventing, reducing the risk of, and delaying the onset of microbial infections in humans and animals.
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Page/Page column 173
(2019/12/28)
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- Studies toward the Total Synthesis of the Marine Macrolide Salarin C
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A convergent strategy for the synthesis of dideoxysalarin C (3) as a potential intermediate for the total synthesis of the marine macrolide salarin C (1) is described. The macrolactone core of 3 was assembled by Suzuki coupling between alkyl iodide 9 and
- Schrof, Raffael,Altmann, Karl-Heinz
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supporting information
p. 7679 - 7683
(2018/12/11)
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- ANTIMICROBIALS AND METHODS OF MAKING AND USING SAME
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The present disclosure relates generally to the field of antimicrobial compounds and to methods of making and using them. These compounds are useful for treating, preventing, reducing the risk of, and delaying the onset of microbial infections in humans a
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Page/Page column 202
(2017/12/13)
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- ANTIMICROBIALS AND METHODS OF MAKING AND USING SAME
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The present disclosure relates generally to the field of antimicrobial compounds and to methods of making and using them. These compounds are useful for treating, preventing, reducing the risk of, and delaying the onset of microbial infections in humans and animals. In some embodiments, the present disclosure provides a compound of Formula (I) or a tautomer thereof or a pharmaceutically acceptable salt of the compound or tautomer.
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Page/Page column 108
(2017/12/13)
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- Pd/C-Cu mediated direct and one-pot synthesis of γ-ylidene butenolides
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10% Pd/C in combination with CuI, PPh3, and Et3N has been identified as an effective catalyst system for the coupling of (Z)-3-iodoacrylic acid with terminal alkynes in 1,4-dioxane leading to the one-pot synthesis of γ-ylidene butenolides. The methodology showed remarkable regio- and stereoselectivity as only the five-membered lactone ring products were formed with an exocyclic double bond possessing Z-geometry.
- Rambabu,Bhavani,Nalivela, Kumara Swamy,Mukherjee, Soumita,Rao, M.V. Basaveswara,Pal, Manojit
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p. 2151 - 2155
(2013/04/24)
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- HYDRAZIDE CONTAINING NUCLEAR TRANSPORT MODULATORS AND USES THEREOF
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The invention generally relates to nuclear transport modulators, e.g., CRM1 inhibitors, and more particularly to a compound represented by structural formula (I): or a pharmaceutically acceptable salt thereof, wherein the values and alternative values for the variables are as defined and described herein. The invention also includes the synthesis and use of a compound of structural formula I, or a pharmaceutically acceptable salt or composition thereof, e.g., in the treatment, modulation and/or prevention of physiological conditions associated with CRM1 activity.
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Page/Page column 88
(2013/03/26)
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- Copper-free Sonogashira coupling of cyclopropyl iodides with terminal alkynes
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The substrate scope of the copper-free Sonogashira coupling has been successfully extended to cyclopropyl iodides, allowing an efficient access to a wide variety of functionalized alkynyl cyclopropanes.(Figure Presented)
- De Carne-Carnavalet, Benoit,Archambeau, Alexis,Meyer, Christophe,Cossy, Janin,Folleas, Benoit,Brayer, Jean-Louis,Demoute, Jean-Pierre
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supporting information; experimental part
p. 956 - 959
(2011/04/25)
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- PREPARATION AND UTILITY OF SUBSTITUTED ALLYLAMINES
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Disclosed herein are substituted allylamines having structural Formula I, processes of preparation thereof, pharmaceutical compositions thereof, and the methods of their use thereof. (I)
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Page/Page column 60-61
(2008/12/06)
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- Extension of the library of biologically active γ-alkylidene butenolides
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γ-Alkylidene butenolides bearing a deoxyriboside, a steroid, and a metallocene moiety were synthesized by stereoselective sequential cross-coupling lactonization procedure from the corresponding functionalized terminal alkynes with 3-iodopropenoic acids.
- Novak, Petr,Pour, Milan,Spulak, Marcel,Votruba, Ivan,Kotora, Martin
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experimental part
p. 3465 - 3472
(2009/05/27)
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- Mechanistic studies on the Heck-Mizoroki cross-coupling reaction of a hindered vinylboronate ester as a key approach to developing a highly stereoselective synthesis of a C1-C7 Z,Z,E,-triene synthon for viridenomycin
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Mechanistic studies of the Heck-Mizoroki reaction of a vinylboronate ester with electronically different (four-substituted) aryl iodides shows that electron donors accelerate the cross-coupling, demonstrating that the oxidative addition step is not rate d
- Batsanov, Andrei S.,Knowles, Jonathan P.,Whiting, Andrew
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p. 2525 - 2532
(2008/02/02)
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- A closer look at the hydroiodination of propiolic acid
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The crystal structures of cis-3-iodoacrylic acid (1), trans-3-iodoacrylic acid (2), trans-3-iodoacrylic acid methyl ester (3), 3,3-diiodopropanoic acid (4), and trans-2,3-diiodoacrylic acid (5) are reported. Compounds 1 and 2 are the kinetic and thermodynamic products, respectively, of the hydroiodination of propiolic acid. Compound 4 results from addition of a second equivalent of hydroiodic acid to 1 or 2, whereas 5 results from the addition of trace elemental iodine to propiolic acid. Copyright Taylor & Francis Group, LLC.
- Donahue, James P.
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p. 3461 - 3471
(2007/10/03)
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- Stereoselective synthesis of trienoic acids: Synthesis of retinoic acids and analogues
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Stereoselective construction of conjugated trienoic acids was achieved through two successive Stille reactions, the first step consisting of the coupling of (E)-1,2-bis(tributylstannyl)ethene and tributylstannyl (Z)- or (E)-3-iodoalk-2-enoates. Two different routes were used for the second step: (1) cross-coupling of the stannyldienoic acid reagents and vinyl iodides, or (2) cross-coupling of vinylstannane reagents and the tributylstannyl 5-iodopenta-2,4-dienoates generated by iododestannylation of stannyldienes. Vinylstannanes synthesized by stannylmetalation of the Negishi dienyne derived from β- or α-ionone and safranal thus provided access to stereodefined retinoic acids. Some retinoid and yne analogues were also prepared by Sonogashira coupling. Georg Thieme Verlag Stuttgart.
- Abarbri, Mohamed,Parrain, Jean-Luc,Duchene, Alain,Thibonnet, Jerome
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p. 2951 - 2970
(2008/02/05)
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- Total synthesis of (+)-brefeldin A
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The total synthesis of (+)-brefeldin A has been accomplished via 15 linear steps in a 7.9% overall yield from the known Weinreb amide 6. The key parts of this approach include the stereoselective construction of the cis-disubstituted hydroxycyclopentane skeleton and the direct introduction of the C1-C3 acrylate moiety using a new variant of a trans-vinylogous acyl anion equivalent.
- Suh, Young-Ger,Jung, Jae-Kyung,Seo, Seung-Yong,Min, Kyung-Hoon,Shin, Dong-Yun,Lee, Yong-Sil,Kim, Seok-Ho,Park, Hyun-Ju
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p. 4127 - 4137
(2007/10/03)
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- A trans-vinylogous ester anion equivalent and its application to the synthesis of (+)-brefeldin A
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A new trans-vinylogous ester anion equivalent which reacts with a variety of carbonyl systems has been developed. In addition, the concise total synthesis of (+)-brefeldin A utilizing facile acylation of this new variant of vinylogous acyl anion equivalent has been accomplished.
- Suh, Young-Ger,Seo, Seung-Yong,Jung, Jae-Kyung,Park, Ok-Hui,Jeon, Ra-Ok
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p. 1691 - 1694
(2007/10/03)
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- An efficient and stereoselective synthesis of xerulin via Pd-catalyzed cross coupling and lactonization featuring (E)-lodobromoethylene as a novel two-carbon synthon.
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[structure: see text] Xerulin, an inhibitor of cholesterol biosynthesis, has been synthesized from commercially available (E)-1-bromopropene, acetylene, and propynoic acid in five steps (longest linear sequence) in 30% overall yield and >96% stereoselectivity. The preparation of (E)-iodobromoethylene and its use in the Pd-catalyzed cross coupling are two of the novel aspects of the synthesis reported herein.
- Negishi,Alimardanov,Xu
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- The formal total synthesis of (±)-strychnine via a cobalt-mediated [2 + 2 + 2]cycloaddition
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(equation presented) A short, highly convergent total synthesis of racemic isostrychnine, and thus strychnine, has been completed. The route involves 14 steps in the longest linear sequence and is highlighted by a cobalt-mediated [2 + 2 + 2]cycloaddition of an alkynylindole nucleus to acetylene.
- Eichberg, Michael J.,Dorta, Rosa L.,Lamottke, Kai,Vollhardt, K. Peter C.
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p. 2479 - 2481
(2007/10/03)
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- A synthetic approach to natural dienamides of insecticidal interest
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An efficient synthesis of dienamides of insecticidal interest has been stereoselectively achieved featuring a Stille cross-coupling reaction as the key step.
- Abarbri, Mohamed,Parrain, Jean-Luc,Duchene, Alain
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p. 239 - 249
(2007/10/03)
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- Substituent Effects in the Intramolecular Diels-Alder Reaction of 6-Furylhexenoates
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The series of furyl enone esters, 4a-c, were synthesized from furan or furfural by straightforward routes. Their thermal intramolecular Diels-Alder reactions to give the tricyclic ketones 5a-c were studied in acetonitrile and toluene at two temperatures and the kinetics of the reactions determined. A comparison of these data with that obtained for the corresponding esters 2 to give the lactones 3 indicates that the rate enhancements seen for the esters (rate of dimethyl 310 times that of monomethyl) are much larger than those seen for the ketones (rate of dimethyl 6.8 times that of monomethyl). Thus, this is additional evidence for the earlier hypothesis that the presence of the oxygen atom in the tether is a factor responsible for the larger than normal rate enhancements.
- Jung, Michael E.,Kiankarimi, Mehrak
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p. 2968 - 2974
(2007/10/03)
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- Highly efficient and selective procedures for the synthesis of γ-alkylidenebutenolides via palladium-catalyzed ene-yne coupling and palladium- or silver-catalyzed lactonization of (Z)-2-en-4-ynoic acids. Synthesis of rubrolides A, C, D, and E
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The diacetates of rubrolides A, C, D, and E (1 a-d) were prepared in modest yields by the Pd-catalyzed cross coupling-lactonization tandem reaction of 5a or 5b with 6a or 6b using Cl2Pd(PPh3)2 and CuI as catalysts. The feasibility of converting the diacetates into rubrolides was demonstrated by the synthesis of rubrolide C by treatment of 1b with methanolic K2CO3 in THF. A detailed investigation of various parameters and conditions has indicated that formation of the corresponding six-membered lactones 7 and/or the cross coupling-lactonization-Heck substitution products 11 can be serious side reactions under non-optimized conditions and that the use of Pd(PPh3)4 rather than phosphine-free complexes, e.g., CI2Pd(PhCN)2, or complexes of low phosphine content, e.g., Cl2Pd(PPh3)2, along with CuI and NEt3 in MeCN provides satisfactory conditions for the cross coupling-lactonization tandem reaction. Thus, the diacetate of rubrolide A (1a) was prepared in 70% isolated yield. The optimized conditions reported herein appear to be generally applicable to the stereoselective and regioselective synthesis of γ-alkylidenebutenolides in a highly efficient manner.
- Kotora, Matin,Negishi, Ei-Ichi
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p. 121 - 128
(2007/10/03)
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- Efficient Synthesis of Conjugated (2E)- or (2Z)-En-4-ynoic Acids and (2E,4E)- or (2Z,4E)-Dienoic Acids via Palladium-Catalysed Cross Coupling
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(E)- or (Z)-Enynoic acids and (2E,4E)- or (2Z,4E)-dienoic acids can be obtained in good yields under mild conditions through palladium-catalysed cross coupling of (E)- or (2)-3-iodoprop-2-enoic acid with alkynylzinc or vinyltin reagents.
- Abarbri, Mohamed,Parrain, Jean-Luc,Cintrat, Jean-Christophe,Duchene, Alain
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- A convenient procedure for the efficient preparation of alkyl (Z)-3-iodo-2-alkenoates
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Reaction of alkyl 2-alkynoates with sodium iodide (1.6-5.5 equiv.) in acetic acid (6.2-13 equiv.) at 115 deg C provides good to excellent yields of the corresponding alkyl (Z)-3-iodo-2-alkenoates.
- Piers, Edward,Wong, Timothy,Coish, Philip D.,Rogers, Christine
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p. 1816 - 1819
(2007/10/02)
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- A Novel Regio- and Stereospecific Hydrohalogenation Reaction of 2-Propynoic Acid and Its Derivatives
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2-Propynoic acid and its derivatives are hydrohalogenated regio- and stereospecifically by reaction with lithium halides in acetic acid, or preferably with 1 equiv of acetic acid in refluxing CH3CN, to afford the thermodynamically unfavorable (Z)-3-halopropenoic acids and their derivatives as sole products.A rationale for the regio- and stereospecifity is briefly discussed.
- Ma, Shengming,Lu, Xiyan,Li, Zhigang
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p. 709 - 713
(2007/10/02)
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- A Novel Stereospecific Hydrohalogenation Reaction of Propiolates and Propiolic Acid
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(Z)-3-Halo-propenoates or -propenoic acids have been synthesized stereospecifically by the reaction of lithium halides in acetic acid with propiolates or propiolic acid, respectively.
- Ma, Shengming,Lu, Xiyan
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p. 1643 - 1644
(2007/10/02)
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- Synthesis and Properties of the Valence Tautomer of cis-Iodosocyclopropanecarboxylic Acid: 4,5-Methano-1-hydroxyiodoxol-3(1H)-one
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4,5-Methano-1-hydroxyiodoxol-3(1H)-one (4) was synthesized from propionic acid in six steps.Key reactions included Simmons-Smith cyclopropanation of cis-3-iodopropen-2-ol, followed by pyridinium dichromate oxidation to cis-iodocyclopropanecarboxylic acid.The final iodo to iodoso oxidation used either chlorination/hydrolysis or peracetic acid procedures.Compound 4 exists in the 1-hydroxyiodoxolone form, not in the "open" cis-cyclopropanecarboxylic acid form (3), as shown by its "high" pKa (7.55) and by its ability to cleave p-(nitrophenyl)diphenyl phosphate(k = 0.0044 s-1) in pH 8 aqueous micellar solution.Compound 4 disproportionates to iodo (5) and iodoxy (7) compounds in pH 8 aqueous buffer with k = 0.027 L/(M*s).Ab initio molecular orbital calculations are described which help rationalize the observed properties of 4.The reactivity of 4 (and related species) is intimately connected to the structure and bonding around the formally hypervalent iodine atom.
- Moss, Robert A.,Wilk, Boguslawa,Krogh-Jespersen, Karsten,Westbrook, John D.
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p. 6729 - 6734
(2007/10/02)
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- Conformational Analysis of Some N-Alkyl-β-halogenoacrylamides
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cis N-Alkyl-β-halogenoacrylamides have an s-skew conformation which is solvent dependent.The more polar the solvent the smaller is the amount of skew in the conformation.The skew angle is also halogen dependent.
- Wojcik, Jacek,Stefaniak, Lech,Witanowski, Michal,Webb, Graham A.
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