- Syntheses of (-)-pelletierine and (-)-homopipecolic acid
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Enantiomeric syntheses of (-)-homopipecolic acid and (-)-pelletierine have been achieved by chiral resolution of tropanol followed by Baeyer-Villiger oxidation. The methodology provides a practical route for the synthesis of optically pure piperidines. The Royal Society of Chemistry 2012.
- Chiou, Wen-Hua,Chen, Guei-Tang,Kao, Chien-Lun,Gao, Yu-Kai
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supporting information; experimental part
p. 2518 - 2520
(2012/04/23)
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- Histamine H3 Inverse Agonists and Antagonists and Methods of Use Thereof
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Provided herein are fused imidazolyl compounds, methods of synthesis, and methods of use thereof. The compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, including, e.g., neurological disorders and metabolic disorders. Compounds provided herein inhibit the activity of histamine H3 receptors and modulate the release of various neurotransmitters, such as, e.g., histamine, acetylcholine, norepinephrine, and dopamine (e.g. at the synapse). Pharmaceutical compositions containing the compounds and their methods of use are also provided herein.
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Page/Page column 59
(2011/04/18)
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- Hydroformylation of alkenylamines. Concise approaches toward piperidines, quinolizidines, and related alkaloids
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Linear hydroformylation of N-protected allyl- or homoallylamines (cyclohydrocarbonylation: CHC), followed by a reductive amination constitute the two key steps toward convenient routes to aza-heterocycles.
- Airiau, Etienne,Girard, Nicolas,Pizzeti, Marianna,Salvadori, Jessica,Taddei, Maurizio,Mann, Andre
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supporting information; experimental part
p. 8670 - 8673
(2011/02/28)
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- Asymmetric synthesis of Sedum alkaloids via lithium amide conjugate addition
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Conjugate addition of lithium (R)-N-allyl-N-(α-methylbenzyl)amide or lithium (R)-N-but-3-enyl-N-(α-methylbenzyl)amide to an alkyl hexa-2,4-dienoate or alkyl hepta-2,6-dienoate, followed by ring-closing metathesis of the olefin functionalities within the resultant β-amino ester, generates a range of diastereoisomerically pure azacycles in good yield. These homochiral templates are readily transformed to a range of piperidine alkaloids of the Sedum family, and the corresponding five-, seven- and eight-membered ring homologues.
- Davies, Stephen G.,Fletcher, Ai M.,Roberts, Paul M.,Smith, Andrew D.
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experimental part
p. 10192 - 10213
(2010/02/28)
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- Improved protocol for asymmetric, intramolecular heteroatom Michael addition using organocatalysis: Enantioselective syntheses of homoproline, pelletierine, and homopipecolic acid
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(Chemical Equation Presented) An improved protocol for the construction of enantioenriched pyrrolidine, indoline, and piperidine rings using an organocatalyzed, intramolecular heteroatom Michael addition is described. Application to the enantioselective synthesis of homoproline, homopipecolic acid, and pelletierine has been accomplished.
- Carlson, Erik C.,Rathbone, Lauren K.,Yang, Hua,Collett, Nathan D.,Carter, Rich G.
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p. 5155 - 5158
(2008/09/21)
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- Substituted Sulfonamide Compounds
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Substituted sulfonamide compounds corresponding to formula I pharmaceutical compositions comprising them, a process for preparing them, and the use of such compounds to treat or inhibit pain and other disorders or disease states.
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Page/Page column 39
(2009/01/24)
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- Synthesis of the quinolizidine alkaloids (-)-lasubine II and (±)-myrtine by conjugate addition and intramolecular acylation of amino esters with acetylenic sulfones
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(Chemical Equation Presented) The conjugate additions of (2-piperidyl)acetate esters to acetylenic sulfones, followed by LDA-promoted intramolecular acylations, afforded cyclic enaminones that were readily converted into the corresponding 4-substituted 2-
- Back, Thomas G.,Hamilton, Michael D.,Lim, Vania J. J.,Parvez, Masood
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p. 967 - 972
(2007/10/03)
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- An efficient synthesis of chiral cyclic β-amino acids via asymmetric hydrogenation
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Cyclic β-amino acids, homoproline, homopipecolic acid and 3-carboxy-methylmorpholine were obtained in high enantiomeric excesses by transition metal-catalyzed asymmetric hydrogenation of cyclic β-acylamino-alkenoates. These compounds were synthesized by a
- Pousset, Cyrille,Callens, Roland,Marinetti, Angela,Larchevêque, Marc
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p. 2766 - 2770
(2007/10/03)
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- Enzymatic resolution of cyclic N-Boc protected β-aminoacids
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Methyl and ethyl esters of N-Boc homoproline, homopipecolic acid and 3-carboxymethyl-morpholine were kinetically resolved by hydrolysis catalysed by Burkholderia cepacia lipase to give the corresponding acids and residual esters in enantiomeric excesses better than 99% (E > 100).
- Pousset, Cyrille,Callens, Roland,Haddad, Mansour,Larcheveque, Marc
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p. 3407 - 3412
(2007/10/03)
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- PROCESS FOR PREPARATION OF PIPERIDIN-2-YLACETIC ACID
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Piperidin-2-ylacetic acid (II) is efficiently and safely produced in industrial scale by treating piperidin-2-ylethanol (I) with 2,2,6,6-tetramethylpiperidin-1-oxyl, sodium hypochlorite and sodium chlorite in a two phase solvent comprising an organic solvent and water without using strongly toxic chromium trioxide.
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- PROCESS FOR THE ENANTIOSELECTIVE PRODUCTION OF AN AMINO ACID DERIVATIVE COMPRISING AT LEAST ONE NITROGENOUS HETEROCYCLE
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Process for the enantioselective production of an amino acid derivative comprising at least one nitrogenous heterocycle, said heterocycle being substituted with at least one side chain comprising a functional group of carboxyl type, such as a carboxyl group, an ester group or an amide group, which process comprises at least one step in which a prochiral unsaturated amino acid derivative of formula (I) is subjected to hydrogenation in the presence of an enantiopure hydrogenation catalyst.
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- Concise total synthesis of (±)-aloperine and 6-epi-aloperine
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(figure presented) Total synthesis of aloperine and 6-epj-aloperine is reported. The crucial steps of the synthetic strategy are an aza-annulation reaction and an intermolecular Diels-Alder reaction. The synthetic plan proceeds from commercially available
- Passarella, Daniele,Angoli, Marco,Giardini, Alessandra,Lesma, Giordano,Silvani, Alessandra,Danieli, Bruno
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p. 2925 - 2928
(2007/10/03)
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- Rearrangement of ammonium ylides produced by intramolecular reaction of catalytically generated metal carbenoids. Part 2. Stereoselective synthesis of bicyclic amines
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Ammonium ylides produced by intramolecular reaction of copper carbenoids tethered to cyclic allylic amines undergo [2,3]-rearrangement to deliver bicyclic amines. The reaction can be performed using a cyclic N-allylamine in which the diazo group is tethered adjacent to nitrogen, or a vinyl-substituted cyclic amine in which the diazo group is N-tethered to the ring. In the former type of reaction, stereoselective ylide formation and rearrangement usually delivers high levels of diastereocontrol. In the latter case, efficient 'chirality transfer' can be accomplished when the reaction is performed using an enantiomerically pure substrate. The reactions have been used to construct pyrrolizidine, indolizidine and quinolizidine systems, and the CE sub-unit found in the manzamine and ircinal alkaloids.
- Clark,Hodgson,Goldsmith,Blake,Cooke,Street
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p. 3325 - 3337
(2007/10/03)
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- Synthesis of optically active 2-piperidylglycine
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Both chiral threo- and erythro-2-piperidylglycines were synthesized from racemic 2-[(N-benzyloxycarbonyl)piperidin-2-yl]ethanoic acid. (4S,5S)-4- Methyl-5-phenyl-2-oxa-zolidinone was used as a chiral auxiliary in the resolution and azidation.
- Chung, Hyun-Kyu,Kim, Hyung-Woo,Chung, Kyoo-Hyun
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p. 2983 - 2989
(2007/10/03)
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- Synthesis and in vitro characterization of new growth hormone secretagogues derived from ipamorelin with dipeptidomimetic N-terminals
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The structural requirements for N-terminal features for the minimal structure of growth hormone secretagogues derived from ipamorelin are investigated. It is found, that incorporation of nonpolar peptidomimetic amino acids at the N-terminal can replace the Aib-His moiety and lead to compounds with high in vitro potency with respect to their growth hormone secretagogue properties. New unnatural amino acids with double bonds, ether- linkages, and 1,3-phenylene-moieties in the backbone proved to be valuable dipeptidomimetics. Using them, growth hormone secretagogues with high potencies were obtained.
- Peschke, Bernd,Ankersen, Michael,Sehested Hansen, Birgit,Kruse Hansen, Thomas,Langeland Johansen, Nils,Lau, Jesper,Madsen, Kjeld,Petersen, Hans,Thogersen, Henning,Watson, Brett
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p. 363 - 380
(2007/10/03)
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- A NOVEL OXIDATIVE RING-OPENING REACTION OF ISOXAZOLIDINES: SYNTHESES OF β-AMINO KETONES AND β-AMINO ACID ESTERS FROM SECONDARY AMINES
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A novel oxidative ring-opening reaction of isoxazolidines upon treatment with an electrophile and subsequently with a base gives β-amino ketones and β-amino acid esters highly efficiently.
- Murahashi, Shun-Ichi,Kodera, Yoichi,Hosomi, Tatsuhide
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p. 5949 - 5952
(2007/10/02)
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- ASYMMETRIC α-AMIDOALKYLATION. SYNTHESIS OF α-SUBSTITUTED PIPERIDINES OF HIGH ENANTIOMERIC PURITY
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A stereoselective α-amidoalkylation was performed employing the chiral and cyclic enamide 1.The resulting amides 6 were employed in the synthesis of the title products.
- Wanner, Klaus Th.,Kaertner, Annerose
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p. 921 - 924
(2007/10/02)
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- Asymmetric α-Amidoalkylation. Syntheses of Enantiomerically Pure α-Substituted Piperidines with 1-Camphanoyl-1,2,3,4-tetrahydropyridine
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In a novel asymmetric synthesis the homochiral enamide 1 is coupled with the silyl enol ethers 5a-c in a diastereoselective fashion to afford the amidoalkylation products 6/7a-c.These are employed in the synthesis of enantiomerically pure, in α-position R
- Wanner, Klaus Th.,Kaertner, Annerose
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p. 1253 - 1267
(2007/10/02)
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- Decarboxylation Reaction. X. Introduction of a Carbon unit at the α-Position of Amines by Reaction of Hexahydro-1,3,5-triazines with Carboxylic Acids
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An efficient method for introducing a carbon unit at the α-position of alicyclic amines is described.The method involves the reaction of monocyclic or tetracyclic hexahydro-1,3,5-triazines with trichloroacetic acid, cyanoacetic acid, malonic acid and their derivatives, which are introduced into the α-position of amines in the decarboxylated form.Keywords --- 1,3,5-trialkylhexahydro-1,3,5-triazine; trimer of alicyclic imine; decarboxylation; β-amino acid; carboxylic acid
- Fukawa, Hidemichi,Terao, Yoshiyasu,Achiwa, Kazuo,Sehiya, Minoru
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