- Close the ring to break the cycle: Tandem quinolone-alkyne-cyclisation gives access to tricyclic pyrrolo[1,2-: A] quinolin-5-ones with potent anti-protozoal activity
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Expanding the chemical space of quinolones led to a tandem quinolone-alkyne-cyclisation reaction allowing chemoselective control of the synthesis of tricyclic pyrrolo[1,2-a]quinolin-5-ones. Importantly, we discovered anti-protozoal activity against Plasmodium and Toxoplasma with specific potency of one of the compounds against the liver stage of the malaria parasite in the nanomolar range.
- Szamosvári, Dávid,Sylvester, Kayla,Schmid, Philipp,Lu, Kuan-Yi,Derbyshire, Emily R.,B?ttcher, Thomas
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Read Online
- Enantioselective allylation of (2E,4E)-2,4-dimethylhexadienal: Synthesis of (5R,6S)-(+)-Pteroenone
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Abstract Allylation, trans- and cis-crotylation of (2E,4E)-2,4-dimethylhexadienal, a representative α,β,γ,δ-unsaturated aldehyde, was carried out under different catalytic and stoichiometric conditions. The reactions catalyzed by organocatalysts TRIP-PA and N,N′-dioxides gave the best results with respect to yields, asymmetric induction, and catalyst load in comparison to other procedures. The developed methodology was applied in the enantioselective synthesis of (5R,6S)-(+)-pteroenone, a defensive metabolite (ichthyodeterrent) of the Antarctic pteropod Clione antarctica. Allylation and crotylation of an α,β,γ,δ-unsaturated aldehyde was studied under various conditions. The asymmetric induction was as high as 96 % ee. The anti-crotylation product was used as the crucial intermediate for the enantioselective synthesis of (5R,6S)-(+)-pteroenone, a defensive metabolite of Clione Antarctica.
- Koukal, Petr,Kotora, Martin
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Read Online
- Total Synthesis of (-)-Hymenosetin
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The 3-decalinoyltetramic acid (-)-hymenosetin and its N-methyl analogue were prepared in 11 and 8 steps, respectively, from (+)-citronellal using an intramolecular Diels-Alder reaction as the key step. This method represents the first example for the synthesis of a 3-decalinoyltetramic acid with a free NH moiety. The stereochemistry of the title compound, an unnatural diastereomer, and of a decalin building block was studied in detail using circular dichroism spectroscopy in the IR and UV/VIS freqeuncy range. This allowed to determine the absolute configuration of the natural product and to plan the synthetic route.
- Kauhl, Ulrich,Andernach, Lars,Weck, Stefan,Sandjo, Louis P.,Jacob, Stefan,Thines, Eckhard,Opatz, Till
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Read Online
- A CONJUGATE OF A TUBULYSIN ANALOG WITH BRANCHED LINKERS
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The present invention relates to the conjugation of a tubulysin analog compound to a cell-binding molecule with branched/side-chain linkers for having better delivery of the conjugate compound and targeted treatment of abnormal cells. It also relates to a branched-linkage method of conjugation of a tubulysin analog molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and autoimmune disease.
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Paragraph 000277; 000278
(2021/03/02)
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- Photoenzymatic Generation of Unstabilized Alkyl Radicals: An Asymmetric Reductive Cyclization
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Flavin-dependent "ene"-reductases can generate stabilized alkyl radicals when irradiated with visible light; however, they are not known to form unstabilized radicals. Here, we report an enantioselective radical cyclization using alkyl iodides as precursors to unstabilized nucleophilic radicals. Evidence suggests this species is accessed by photoexcitation of a charge-transfer complex that forms between flavin and substrate within the protein active site. Stereoselective delivery of a hydrogen atom from the flavin semiquinone to the prochiral radical formed after cyclization provides high levels of enantioselectivity across a variety of substrates. Overall, this transformation demonstrates that photoenzymatic catalysis can address long-standing selectivity challenges in the radical literature.
- Clayman, Phillip D.,Hyster, Todd K.
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supporting information
p. 15673 - 15677
(2020/10/18)
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- Preparation method of zeatin
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The invention provides a preparation method of zeatin, which relates to the technical field of organic synthesis, the preparation method comprises the following steps: reducing 6-trans-(3-methyl-2-alkene-4-butyrate)group-aminopurine to prepare zeatin; according to the brand-new zeatin synthesis route provided by the invention, 6-trans-(3-methyl-2-alkene-4-butyrate)-aminopurine is used as a raw material, is a relatively good solid, is easy to treat, relatively few in synthesis route steps, relatively high in yield and easy to produce and amplify, and further can realize industrial production.
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Paragraph 0059-0061
(2020/09/23)
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- REGULATING PLANT GROWTH USING A DIAPOCAROTENOID
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Embodiments of the present disclosure describe diapocarotenoid plant growth regulators represented by formula (I): R-A-R (I) or a precursor, salt, solvate, stereoisomer or polymorph thereof; wherein R is a monovalent carbonyl moiety selected from the group consisting of aldehydes, ethers, diethers, carboxylic acids, alcohols, and ester carboxylates and A is a bivalent polyene represented by the bivalent moiety -(CRa=CRb)x- wherein x is the number of double bonds in polyene moiety A, and Ra and Rb are, independently, hydrogen, a hydrocarbon, or an alkoxy group, and composition of the diapocarotenoid plant growth regulators in an agronomically acceptable carrier. Methods of regulating plant growth including promoting root development, increasing nutrient uptake, enhancing resistance to abiotic stress factors, invigorating plant growth, increasing plant yield, and increasing plant biomass by applying at least one diapocarotenoid plant growth regulator to a seed, plant propagation material, plant or plant growth medium are also described.
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Paragraph 00117
(2019/10/15)
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- Metal-Free Transfer Hydroiodination of C-C Multiple Bonds
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The design and a gram-scale synthesis of a bench-stable cyclohexa-1,4-diene-based surrogate of gaseous hydrogen iodide are described. By initiation with a moderately strong Br?nsted acid, hydrogen iodide is transferred from the surrogate onto C-C multiple bonds such as alkynes and allenes without the involvement of free hydrogen iodide. The surrogate fragments into toluene and ethylene, easy-to-remove volatile waste. This hydroiodination reaction avoids precarious handling of hydrogen iodide or hydroiodic acid. By this, a broad range of previously unknown or difficult-to-prepare vinyl iodides can be accessed in stereocontrolled fashion.
- Chen, Weiqiang,Walker, Johannes C. L.,Oestreich, Martin
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supporting information
p. 1135 - 1140
(2019/01/11)
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- A CONJUGATE OF A TUBULYSIN ANALOG WITH BRANCHED LINKERS
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The present invention relates to the conjugation of a tubulysin analog compound to a cell-binding molecule with branched/side-chain linkers for having better delivery of the conjugate compound and targeted treatment of abnormal cells. It also relates to a branched-linkage method of conjugation of a tubulysin analog molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and autoimmune disease.
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Page/Page column 10; 164-165
(2019/07/17)
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- Asymmetric Reductive Carbocyclization Using Engineered Ene Reductases
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Ene reductases from the Old Yellow Enzyme (OYE) family reduce the C=C double bond in α,β-unsaturated compounds bearing an electron-withdrawing group, for example, a carbonyl group. This asymmetric reduction has been exploited for biocatalysis. Going beyond its canonical function, we show that members of this enzyme family can also catalyze the formation of C?C bonds. α,β-Unsaturated aldehydes and ketones containing an additional electrophilic group undergo reductive cyclization. Mechanistically, the two-electron-reduced enzyme cofactor FMN delivers a hydride to generate an enolate intermediate, which reacts with the internal electrophile. Single-site replacement of a crucial Tyr residue with a non-protic Phe or Trp favored the cyclization over the natural reduction reaction. The new transformation enabled the enantioselective synthesis of chiral cyclopropanes in up to >99 % ee.
- Heckenbichler, Kathrin,Schweiger, Anna,Brandner, Lea Alexandra,Binter, Alexandra,Toplak, Marina,Macheroux, Peter,Gruber, Karl,Breinbauer, Rolf
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p. 7240 - 7244
(2018/06/15)
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- Regio- and Stereoselective Nickel-Catalyzed Coupling of Boronic Acids with Allenoates
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The Ni(II)-catalyzed cross-coupling of arylboronic acids with allenoates is documented. The high regio- and stereoselectivity of the process enables a wide range of β-aryl β,γ-unsaturated esters to be prepared in good to excellent yields (up to 95%) and high E / Z -selectivity. Additionally, [3+2]-cascade sequence was observed when 2-formylphenylboronic acid was employed.
- Liu, Yang,Daka, Mario,Bandini, Marco
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p. 3187 - 3196
(2018/08/17)
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- BIPOLAR TRANS CAROTENOID SALTS AND USES THEREOF
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PROBLEM TO BE SOLVED: To provide compounds useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans. SOLUTION: There is provided a compound which has a structure represented by YZ-TCRO-ZY and is not trans sodium crocetinate [where, Y is a cation; Z is a polar group which is associated with the cation; and TCRO is trans carotenoid skeleton], and preferably, Y is a monovalent metal ion selected from the group consisting of Na+, K+ and Li+, or is an organic cation selected from the group consisting of R4 N+ and R3S+ [R is H, or CnH2n+1(n is 1 to 10)]. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT
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- Synthetic method of Wittig reagent
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The invention discloses a synthetic method of a Wittig reagent. The synthetic method comprises the following steps: (1) by taking alpha-halogenated-ester and triarylphosphine as raw materials, carrying out reaction in a two-phase solvent in presence of a halogenated metal salt catalyst, splitting phase after reaction is finished, recycling and reusing an organic phase, crystallizing an aqueous phase to obtain quaternary phosphonium salt, and recycling and reusing mother liquid; and (2) carrying out reaction on the quaternary phosphonium salt obtained in the step (1) in the aqueous phase in presence of an alkali reagent, and cooling and crystallizing after reaction is finished, so that the Wittig reagent product is obtained. The synthetic method disclosed by the invention has the advantagesthat the whole reaction process and conditions are mild, operation is easy, yield is high, cost is low, and amount of three wastes is less, so that the synthetic method disclosed by the invention isapplicable to industrial production.
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Paragraph 0034; 0035; 0038; 0039; 0041; 0042; 0045; 0046
(2018/03/24)
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- Nickel-catalyzed, ligand-free, diastereoselective synthesis of 3-methyleneindan-1-ols
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Nickel-catalyzed, highly diastereoselective annulations between activated allenes and 2-acetylarylboronic acid or 2-formylarylboronic acids are reported. No ligand for nickel is required, and the reactions proceed efficiently at room temperature to give a broad range of substituted 3-methyleneindan-1-ols. Preliminary results of an enantioselective variant are also described.
- Panchal, Heena,Clarke, Christopher,Bell, Charles,Karad, Somnath Narayan,Lewis, William,Lam, Hon Wai
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supporting information
p. 12389 - 12392
(2018/11/20)
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- PROCESS FOR THE PREPARATION OF SOFOSBUVIR
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A process for the preparation of intermediates 9, useful in the synthesis of sofosbuvir, as well as intermediates of formula [12] are disclosed herein.
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Page/Page column 21
(2017/06/09)
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- BIPOLAR TRANS CAROTENOID SALTS AND THEIR USE
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PROBLEM TO BE SOLVED: To provide trans carotenoid salt compounds useful for improving the diffusibility of oxygen between red blood cells and a body tissue in mammalian including human being, a method for producing them, a method for solubilizing them, and a method for using them. SOLUTION: There are provided compounds represented by the following formula, and are compounds not being trans sodium crocetinate: YZ-TCRO-ZY[Y denotes a cation; Z denotes a polar group coupled to the cation; TCRO denotes a trans carotenoid skeleton; preferably, as follows; Y denotes the monovalent metal ion of Na+,K+ or Li+ or R4 N+ or R3S+;R denotes H or CnH2n+1;n denotes the integer of 1 to 10;Z denotes a carboxyl group, a sulfuric acid group, a mono-phosphoric acid group, a di-phosphoric acid group, or a tri-phosphoric acid group; and TCRO denotes a group using isopronoid in which the single bond and double bond of straight chain carbon and carbon as exemplified by the following formula is repeated (X respectively independently denotes H, a straight chain/branched carbon chain substituted/non-substituted with 1 to 10C halogen or a halogen)]. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPO&INPIT
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- five Yuan fragrance heterocyclic structure containing the anti-hepatitis c compound and its preparation and use
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The invention discloses an anti-HCV (hepatitis C) compound containing a five-membered heteroaromatic ring structure, as well as a preparation method and applications thereof. The compound has a structure shown as the formula I, the compound has excellent anti-HCV virus activity, can be used for preparing anti-HCV drugs, the prepared drugs can be applied by adopting oral administration, intravenous injection or intramuscular injection.
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Paragraph 0087; 0113-0114
(2016/11/21)
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- Efficient and regioselective one-pot synthesis of S-vinyl dithiocarbamates from electron-deficient allenes, amines and CS2
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A novel and efficient one-pot procedure for the synthesis of S-vinyl dithiocarbamates from electron-deficient allenes, amines and CS2was presented. The reactions proceed at room temperature for 10–30?min without any catalyst to afford the products in high yields, excellent regioselectivity and stereoselectivity.
- Li, Ridong,Leng, Penglin,Liu, Bin,Wang, Xin,Ge, Zemei,Li, Runtao
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supporting information
p. 5707 - 5712
(2016/08/23)
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- Ethoxy-formyl subethyl triphenylphosphine preparation method
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The invention relates to a preparation method of (carbethoxyethylidene)triphenylphosphorane. According to the method, after a reaction of triphenyl phosphine and ethyl 2-bromopropionate is completed in a solvent, the reaction products are not required to
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Paragraph 0026; 0027; 0034
(2016/10/08)
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- Preparation method for 3,5-dibenzoyl-2-deoxy-2-fluoro-2-methyl-D-ribono-gamma-lactone
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The invention discloses a preparation method for 3,5-dibenzoyl-2-deoxy-2-fluoro-2-methyl-D-ribono-gamma-lactone. The preparation method comprises the following steps: subjecting a starting raw material D-mannitol to acetone protection and sodium periodate oxidation; then subjecting the treated D-mannitol and a self-made ylide reagent to the Witting reaction; then carrying out selective oxidation by using an aqueous sodium permanganate solution; then successively carrying out sulfonylation, fluorination with potassium fluoride, and ring closing with a concentrated protective group protective group; protecting the hydroxyl group by using benzoyl chloride; and then carrying out purification so as to obtain the final product 3,5-dibenzoyl-2-deoxy-2-fluoro-2-methyl-D-ribono-gamma-lactone. The preparation method provided by the invention uses easily available and cheap raw materials, so production cost is greatly reduced; and the operation of the preparation method is coherent and simple, and the quantity of waste gas, waste water and industrial residues is lower than the quantity of waste gas, waste water and industrial residues reported in the prior art.
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Paragraph 0030; 0050
(2017/06/02)
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- Α-calbonyl phosphorane manufacturing method
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PROBLEM TO BE SOLVED: To provide a new method for producing α-carbonyl phosphorane, which is industrially advantageous, and which brings about a high yield and high purity with a simple operation. SOLUTION: In the reaction to synthesize an α-carbonyl phosphorane represented by general formula (I) by making a base act on an aqueous solution of an α-carbonyl phosphonium salt represented by general formula (II), the crystal of the α-carbonyl phosphorane is easily deposited by conducting the reaction with previous addition of a water-insoluble organic solvent (in formulas, Ar represents an optionally substituted aryl group, R1represents a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aryl group, R2represents an optionally substituted alkyl group or an optionally substituted aryl group, and X-represents a counter anion). COPYRIGHT: (C)2012,JPOandINPIT
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Paragraph 0029
(2016/12/22)
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- Stereoselective olefination of N-sulfonyl imines with stabilized phosphonium ylides for the synthesis of electron-deficient alkenes
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An unprecedented protocol has been developed for thestereoselective synthesis of structurally diverse electron-deficient alkenes in moderate to excellent yields from readily accessible N-sulfonyl imines and stabilized phosphonium ylides. Significantly, the olefination reaction of N-sulfonylimines with nitrile-stabilized phosphonium ylides affords an array of α,β-unsaturated nitriles with high Z selectivity, and the reactions with ester-, amide-, and ketone-stabilized phosphonium ylides afford α,β-unsaturated esters, amides, and ketones with high E selectivity, respectively. Spectroscopic analysis of the reaction mixtures and trapping of the intermediates allow plausible mechanisms to be proposed. Initialimine/ylide addition leads to the formation of betaines that cyclize to form 1,2-azaphosphetanes that subsequently eliminate iminophosphoranes to yield alkenes. For the synthesis of electron-deficient 1,2-disubstituted alkenes, the presence of an electron-withdrawing group in the betaine allows rapid interconversion between its two diastereomers through proton transfer. The Z/E selectivity for alkene synthesis is determined by the different rates at which the two betaine diastereomers form the corresponding 1,2-azaphosphetane diastereomers. In contrast, the Z/E selectivity for the synthesis of electron-deficient trisubstituted alkenes originates from the diastereoselective addition of stabilized phosphonium ylides to N-sulfonyl imines.
- Fang, Fan,Li, Yuan,Tian, Shi-Kai
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supporting information; experimental part
p. 1084 - 1091
(2011/04/15)
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- Total synthesis of (+)-papulacandin D
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A total synthesis of (+)-papulacandin D has been achieved in 31 steps, in a 9.2% overall yield from commercially available materials. The synthetic strategy divided the molecule into two nearly equal sized subunits, the spirocyclic C-arylglycopyranoside and the polyunsaturated fatty acid side-chain. The C-arylglycopyranoside was prepared in 11 steps in a 30% overall yield from triacetoxyglucal. The fatty acid side-chain was also prepared in 11 steps in a 30% overall yield from geraniol. The key strategic transformations in the synthesis are: (1) a palladium-catalyzed, organosilanolate-based cross-coupling reaction of a dimethylglucal-silanol with an electron-rich and sterically hindered aromatic iodide and (2) a Lewis-base catalyzed, enantioselective allylation reaction of a dienal and allyltrichlorosilane. A critical element in the successful execution of the synthesis was the development of a suitable protecting group strategy that satisfied a number of stringent criteria.
- Denmark, Scott E.,Kobayashi, Tetsuya,Regens, Christopher S.
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supporting information; experimental part
p. 4745 - 4759
(2010/08/06)
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- Unprotected vinyl aziridines: Facile synthesis and cascade transformations
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(Figure presented) Functionalized vinylaziridines, readily available from water-stable aziridine aldehydes have led to the construction of a variety of stereochemically rich heterobicycles. A cascade ring-opening/ring-contraction mechanism operates In the course of the process. These results underscore the notion that Interesting and useful nitrogen-mediated relay processes can arise when elements of strain are merged with the manifolds of enamine/iminium ion reactivity.
- Baktharaman, Sivaraj,Afagh, Nicholas,Vandersteen, Adelle,Yudin, Andrei K.
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supporting information; experimental part
p. 240 - 243
(2010/03/24)
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- Methods for synthesis of carotenoids, including analogs, derivatives, and synthetic and biological intermediates
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A method for synthesizing intermediates for use in the synthesis of carotenoid synthetic intermediates, carotenoid analogs, and/or carotenoid derivatives. The carotenoid analog, derivative, or intermediate may be administered to a subject for the inhibition and/or amelioration of any disease that involves production of reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals. In some embodiments, the invention may include methods for synthesizing chemical compounds including an analog or derivative of a carotenoid. Carotenoid analogs or derivatives may include acyclic end groups. In some embodiments, a carotenoid analog or derivative may include at least one substituent. The substituent may enhance the solubility of the carotenoid analog or derivative such that the carotenoid analog or derivative at least partially dissolves in water.
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Page/Page column 36; 14
(2008/12/08)
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- METHODS FOR SYNTHESIS OF CHIRAL INTERMEDIATES OF CAROTENOIDS, CAROTENOID ANALOGS, AND CAROTENOID DERIVATIVES
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A method used for synthesizing intermediates for use in the synthesis of carotenoids and carotenoid analogs, and/or carotenoid derivatives. In some embodiments, the invention includes methods for synthesizing optically active intermediates useful for the synthesis of optically active carotenoids.
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Page/Page column 43-44
(2010/10/20)
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- BIPOLAR TRANS CAROTENOID SALTS AND THEIR USES
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The invention relates to trans carotenoid salt compounds, methods for making them, methods for solubilizing them and uses thereof. These compounds are useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans.
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Page/Page column 26
(2008/06/13)
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- Bipolar trans carotenoid salts and their uses
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The invention relates to trans carotenoid salt compounds, methods for making them, methods for solubilizing them and uses thereof. These compounds are useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans.
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- INHIBITORS OF HUMAN TUMOR-EXPRESSED CCXCKR2
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Pharmaceutical compositions containing organic compounds or salts thereof that serve as modulators for the SDF-1 or I-TAC chemokines are disclosed. The compounds and compositions are useful in the treatment of cancer, especially in the inhibition of cancer proliferation, growth, and metastasis. Methods of interfering with SDF-1 and/or I-TAC binding to the CCXCKR2 receptor and treating cancer using the compounds and pharmaceutical compositions of the present invention are also disclosed.
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- Total Synthesis of (-)-C34-Botryococcene, the Principal Triterpenoid Hydrocarbon of the Freshwater Alga Botryococcus braunii
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The hydrocarbon (-)-C34-botryococcene 1 has been synthesized in enantiomerically pure form by coupling the alkylcopper species 41 to each terminus of diiodide 37.The former was prepared from (2S)-3-hydroxy-2-methylpropionate 2 which was first converted into the alcohol 7.Coupling of the dianion of 7, obtained by deprotonation with the Schlosser base, with tosyl ester 11 gave the alcohol 12 and thence iodide 39.The central segment 37 of the botryococcene chain was synthesized from (2R)-3-hydroxy-2-methylpropionate 15 and entailed a novel rearrangement of the derived αβ-unsatured MOM ester 23 to establish the quaternary allylic centre at C-13.The pair of stereoisomeric hydroxy esters 24 and 25 obtained from this rearrangement were independently advanced to stereochemical convergence at 29, which was subsequently transformed into diiodide 37.The route of synthesis confirms the previous assignment of absolute configuration made to botryococcene 1 at five of the six stereogenic centres, i.e. (3S,7S,10R,16S,20S).
- White, James D.,Reddy, G. Nagabushana,Spessard, Gary O.
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p. 759 - 768
(2007/10/02)
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- Facile synthesis of (-)-serricornin by means of palladium-catalyzed hydrogenolysis of alkenyloxiranes
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Chiral synthesis of (-)-serricornin by using palladium-catalyzed stereoselective hydrogenolysis of the alkenyloxirane to the homoallylic alcohol with formic acid as a key step was carried out.
- Shimizu,Hayashi,Ide,Oshima
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p. 2991 - 2998
(2007/10/02)
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- Use of the Diazoalkane-thione Reaction in the Synthesis of a Vinyltrimethylenemethane Precursor
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Previous studies have shown that the reaction of diazoalkanes with 3,5-dihydro-3,3,5,5-tetramethylpyrazole-4-thione (6) provide a flexible route for the synthesis of precursors to trimethylenemethane (TMM) (1) and tetramethylene-ethane (TME) (2) biradicals.We now show that this route can be adapted for the synthesis of a precursor to another type of non-Kekule polyene, a vinyl-TMM biradical (3).The thermal isomerisation of 1-(2,4-dimethylpent-1-en-3-ylidene)-2,2,3,3-tetramethylcyclopropane (27) to 4-isopropyl-3-isopropylidene-2,5-dimethylhexa-1,4-diene (11) which involves a vinyl-TMM intermediate (3-isopropyl-4-isopropylidene-2,5-dimethylhex-2-ene-1,5-diyl) was shown by deuterium labelling to involve a 1,6-hydrogen shift.It is suggested that such sigmatropic rearrangements of non-Kekule polyenes may involve orbital symmetry control.Related examples are discussed.Two reactions discovered incidentally in the course of this work are of some interest, one involving the synthesis of an allylic amine through the thermal rearrangement of an aziridine (2-isopropyl-3,3-aziridine) (16) and the other the formation of an oxathiole (20) through the reaction of a thione (6) and an α-diazo ketone (3-diazo-4-methylpentan-2-one) (18).
- Bushby, Richard,Mann, Stephen
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p. 2497 - 2504
(2007/10/02)
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