- A short synthesis of lennoxamine via ynamides
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Lennoxamine was synthesized in eight steps from 2,3-dimethoxybenzoic acid via an intermediate ynamide by using palladium-catalyzed Heck-Suzuki-Miyaura domino reactions.
- Couty, Sylvain,Meyer, Christophe,Cossy, Janine
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- Synthetic approaches to pallimamine and analogues using direct imine acylation
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The use of Direct Imine Acylation (DIA) methodology for the total synthesis of pallimamine is described, with three different synthetic routes examined. The construction of three advanced δ-lactam precursors, all utilising DIA, is described, along with attempts to progress these compounds further, using three distinct desymmetrisation strategies, two involving alcohol-aryl coupling, and a third involving an unusual diastereoselective lactonisation.
- Ronson, Thomas O.,Kitsiou, Christiana,Unsworth, William P.,Taylor, Richard J.K.
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p. 6099 - 6106
(2016/09/14)
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- Microwave-assisted domino hydroformylation/cyclization reactions: Scope and limitations
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Hydroformylation of alkenes can be carried out in short time and with low syngas pressure under microwave (MW) dielectric heating. Alkenes, carrying O-, N-, or C-nucleophilic fragments, can be designed for domino reactions, mainly cyclocondensations. Ally
- Airiau, Etienne,Chemin, Claire,Girard, Nicolas,Lonzi, Giacomo,Mann, Andre,Petricci, Elena,Salvadori, Jessica,Taddei, Maurizio
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experimental part
p. 2901 - 2914
(2010/10/21)
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- Synthesis of isoindolobenzazepine alkaloids based on radical reactions or Pd(0)-catalyzed reactions
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(Chemical Equation Presented) Methods for synthesis of a ring system characteristic of isoindolobenzazepine alkaloids were studied. Synthesis of lennoxamine and a formal synthesis of chelenine were accomplished in a short route via radical or Pd(0)-cataly
- Onozaki, Yu,Kurono, Nobuhito,Senboku, Hisanori,Tokuda, Masao,Orito, Kazuhiko
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experimental part
p. 5486 - 5495
(2009/12/06)
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- Structure-activity relationship studies of phenanthridine-based Bcl-X L inhibitors
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Despite their structural similarities, the natural products chelerythrine (5) and sanguinarine (6) target different binding sites on the pro-survival Bcl-XL protein. This paper details the synthesis of phenanthridine-based analogues of the natu
- Bernardo, Paul H.,Wan, Kah-Fei,Sivaraman, Thirunavukkarasu,Xu, Jin,Moore, Felicity K.,Hung, Alvin W.,Mok, Henry Y. K.,Yu, Victor C.,Chai, Christina L. L.
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experimental part
p. 6699 - 6710
(2009/10/23)
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- Synthesis of 3-(arylmethylene)isoindolin-1-ones from ynamides by Heck-Suzuki-Miyaura domino reactions. Application to the synthesis of lennoxamine
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Substituted 3-(arylmethylene)isoindolin-1-ones can be efficiently synthesized from various ynamides and boronic acids by palladium-catalyzed Heck-Suzuki-Miyaura domino reactions. This methodology has been applied to the total synthesis of lennoxamine and a concise route to this isoindolobenzazepine alkaloid was achieved in eight steps from 2,3-dimethoxybenzoic acid via a key intermediate ynamide.
- Couty, Sylvain,Liegault, Beno?t,Meyer, Christophe,Cossy, Janine
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p. 3882 - 3895
(2007/10/03)
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- Dual inhibitors of adipocyte fatty acid binding protein and keratinocyte fatty acid binding protein
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Compounds that are dual aP2/k-FABP inhibitors are provided having the formula wherein A, B, X, Y, R1, R2 and R3 are as described herein. A method is also provided for treating diabetes and related diseases, especially Type II diabetes, employing dual aP2/k-FABP inhibitors alone or in combination with at least one other antidiabetic agent such as metformin, glyburide, troglitazone and/or insulin.
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Page column 66
(2010/02/06)
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- Synthesis of (+/-)-8-Oxotetrahydropalmatine and (+/-)-Gusanlung B
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The 8-oxotetrahydroprotoberberine alkaloids (+/-)-8-oxotetrahydropalmatine and (+/-)-gusanlung B have been synthesized by radical-initiated 1,6-cyclization of the corresponding 2-arylcarbonyl-1-methylenetetrahydroisoquinolines.
- Nimgirawath, Surachai,Ponghusabun, Ong-ard
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p. 951 - 956
(2007/10/02)
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- N-bromosuccinimide/dibromodimethylhydantoin in aqueous base: A practical method for the bromination of activated benzoic acids
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A new bromination method employing NBS or dibromodimethylhydantoin in aqueous base is described for the synthesis of 3-bromo-2,6-dimethoxybenzoic acid (1) and other monobrominated alkoxybenzoic acids.
- Auerbach, Joseph,Weissman, Steven A.,Blacklock, Thomas J.,Angeles, Marshall R.,Hoogsteen, Karst
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p. 931 - 934
(2007/10/02)
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- 3-ETHOXY-2-HYDROXYBENZALDEHYDE AS A STARTING COMPOUND FOR SYNTHESIS OF ISOQUINOLINE ALKALOIDS
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3-Ethoxy-2-hydroxybenzaldehyde (I) was used to prepare 6-bromo-2,3-dihydroxybenzaldehyde (V), 6-bromo-2,3-methylenedioxybenzaldehyde (VIa), 6-bromo-2,3-methylenedioxybenzoic acid (VIIa), and for new synthesis of compounds II, IIIa, IIIb, IV, VIb, VIIb, VIIIa, VIIIb, IXa and IXb.
- Smidrkal, Jan
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p. 2140 - 2144
(2007/10/02)
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