- Synthesis of functionalized pyrrolidin-2-ones and (S)-vigabatrin from pyrrole
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Starting from pyrrole, the novel 3,4-didehydropyrohomoglutamate 8 or (ent)-8 can be efficiently synthesized in up to 91% ee, which can be utilized as a versatile building block toward functionalized pyrrolidin-2-ones. Moreover, (ent)-8 can be readily converted to (S)-Vigabatrin, being an irreversible inhibitor for GABA-T, which is used as adjunctive therapy in patients that suffer from epilepsy.
- Gheorghe, Alexandru,Schulte, Michael,Reiser, Oliver
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- NOVEL FUNCTIONALIZED LACTAMS AS MODULATORS OF THE 5-HYDROXYTRYPTAMINE RECEPTOR 7 AND THEIR METHOD OF USE
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Described herein are new, selective modulators of the 5 -HT7 receptor. These selective compounds can be useful for the treatment of CNS and non-CNS indications. Compounds described herein can be selective in targeting 5-HT7 receptors
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Paragraph 000729-000730
(2021/05/21)
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- NOVEL FUNCTIONALIZED LACTAMS AS MODULATORS OF THE 5-HYDROXYTRYPTAMINE RECEPTOR 7 AND THEIR METHOD OF USE
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Pharmaceutical compositions of the invention comprise functionalized lactam derivatives of formula (I) having a disease-modifying action in the treatment of diseases associated with dysregulation of 5- hydroxytryptamine receptor 7 activity. A is selected
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Paragraph 01136; 01137
(2019/11/28)
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- An asymmetric total synthesis of martinellic acid
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We describe an asymmetric total synthesis of the pyrrolo[3,2-c]quinoline natural product martinellic acid starting from pyrroglutamic acid. A convergent strategy involving a Pd-catalyzed aryl amination reaction of a chiral, non-racemic pyrrolidine derivative incorporates the C2-chiral center which controls the remaining two stereocenters. Elaboration of this adduct through a Grieco-elimination sets the stage for a diastereoselective intramolecular [3+2] azomethine ylide-alkene cycloaddition and the construction of the remaining two chiral centers. Elaboration of the cycloadduct and incorporation the prenyl guanidine units delivered martinellic acid after removal of the protecting groups.
- Badarinarayana, Vivek,Mahmud, Hossen,Lovely, Carl J.
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p. 1082 - 1105
(2019/11/14)
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- Total synthesis of (-)-martinellic acid
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An enantioselective formal total synthesis of the pyrrolo[3,2-c]quinoline natural product martinellic acid has been achieved. The key steps involve a Pd-catalyzed aryl amidation reaction of a pyrroglutamate derivative, an intramolecular [3+2] azomethine ylide-alkene cycloaddition and a reductive ring opening reaction.
- Badarinarayana, Vivek,Lovely, Carl J.
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p. 2607 - 2610
(2007/10/03)
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- Total synthesis of (+)-batzelladine A and (-)-batzelladine D via [4 + 2]-annulation of vinyl carbodiimides with N-alkyl imines
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A diastereoselective [4 + 2]-annulation of vinyl carbodiimides with chiral N-alkyl imines has been developed to access the stereochemically rich polycyclic guanidine cores of the batzelladine alkaloids. Application of this strategy, together with additional key steps such as long-range directed hydrogenation and diastereoselective intramolecular iodo-amination, led to highly convergent total syntheses of (-)-batzelladine D and (+)-batzelladine A with excellent stereocontrol.
- Arnold, Michael A.,Day, Kenneth A.,Duron, Sergio G.,Gin, David Y.
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p. 13255 - 13260
(2008/03/11)
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- Enantioselective Synthesis of (5R,9R)-5-Propyl-octahydroindolizine
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A versatile and practical synthesis of the dendrobatid alkaloid 167B is described using a chiral amino acid as starting material.
- Fleurant, Anne,Celerier, Jean Pierre,Lhommet, Gerard
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p. 695 - 696
(2007/10/02)
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