- Diastereoselective syntheses of new analogues of the farnesyltransferase inhibitor RPR 130401
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The access to several benzo[f]perhydroisoindolic analogues of farnesyltransferase inhibitors from a single dienic precursor is reported. An initial [4 + 2] cycloaddition between diphenylisobenzofuran 6 and pyrrolines 11, 14, and 15 led to either the syn o
- Pichon, Nicolas,Harrison-Marchand, Anne,Mailliet, Patrick,Maddaluno, Jacques
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Read Online
- IMIDAZOPYRIDINE DERIVATIVES AS MODULATORS OF TNF ACTIVITY
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A series of imidazo[l,2-a]pyridine derivatives of formula (I), being potent modulators of human TNFa activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.
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Page/Page column 143
(2014/02/15)
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- A rapid catalytic asymmetric synthesis of 1,3,4-trisubstituted pyrrolidines
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The asymmetric synthesis of 1,3,4-trisubstituted pyrrolidines was accomplished in two steps from readily available starting materials. A 1,3-dipolar cycloaddition of an azomethine ylide to a propiolate ester followed by a Rh-catalyzed asymmetric 1,4-arylation of the resulting pyrroline with an arylboronic acid provided the desired 1,3,4-trisubstituted pyrrolidine products in good to excellent enantioselectivities.
- Belyk, Kevin M.,Beguin, Charlotte D.,Palucki, Michael,Grinberg, Nelu,DaSilva, Jimmy,Askin, David,Yasuda, Nobuyoshi
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p. 3265 - 3268
(2007/10/03)
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- Synthesis of oxa-bridged analogues of farnesyltransferase inhibitor RPR 115135
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Two synthetic routes to new oxygen-bridged analogues of farnesyltransferase inhibitors are described that follow either a [3 + 2]/[4 + 2] or a [4 + 2]/[3 + 2] sequence of reactions. The first approach has been achieved by reacting the in situ generated phenylisobenzofuran (PIBF) 4 with pyrroline 5a and has led stereoselectively to racemic 18, which was transformed in a few steps into the target molecule 2. The second pathway relies on a key intermediate 6, obtained either by condensation of PIBF with methyl acrylate, followed by a deprotonation/selenation and an oxidation/elimination sequence, or by cycloaddition between PIBF and α-phenylselenoacrylate 11, followed by the same oxidation/elimination sequence. The reaction of 6 with amino dipole 7 gives diastereoselective access to pyrrolidine 25, a precursor of the second target 3, an epimer of 2.
- Martin,Mailliet,Maddaluno
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p. 3797 - 3805
(2007/10/03)
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- Trifluoroacetic Acid-Catalyzed 1,3-Cycloaddition of the Simplest Iminium Ylide Leading to 3- or 3,4-Substituted Pyrrolidines and 2,5-Dihydropyrroles
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The 1,3-dipolar cycloaddition of an intermediary iminium ylide formed from N-benzyl-N-(methoxymethyl)trimethylsilylmethylamine to conjugated olefinic and acetylenic dipolarophiles in the presence of a catalytic amount of trifluoroacetic acid has been found to give 3- or 3,4-substituted pyrrolidines and 2,5-dihydropyrroles.
- Terao, Yoshiyasu,Kotaki, Hiromi,Imai, Nobuyuki,Achiwa, Kazuo
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p. 2762 - 2766
(2007/10/02)
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- Synthetic Application of Cyanoaminosilanes as Azomethine Ylide Equivalents
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A series of α-cyanoaminosilanes have been found to act as azomethine ylide equivalents.Treatment of these compounds with silver fluoride in the presence of electron-dificient alkynes and olefins gives substituted pyrroles and pyrrolidines in high yield.It was found that N-benzyl-N-(cyanomethyl)-N-amine undergoes stereospecific cycloaddition with dimethyl fumarate and maleate.The stereospecificity of the reaction is consistent with a concerted cycloaddition reaction.The cycloaddition behavior of an unsymmetrically substituted α-cyanosilylamine with methyl propiolate was also examined and found to react with high overall regioselectivity.The synthetic utility of cyanoaminosilanes as azomethine ylide equivalents was demonstrated by the preparation of a Reniera isoindole alkaloid.The key step in the synthesis involved the reaction of 2-methyl-3-methoxyquinone with N-methyl-N-(cyanomethyl)-N-amine in the presence of silver fluoride to give 2,5-dimethyl-6-methoxy-2H-isoindole-4,7-dione in good yield.
- Padwa, Albert,Chen, Yon-Yih,Dent, William,Nimmesgern, Hildegard
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p. 4006 - 4014
(2007/10/02)
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