• Bulletin of the Korean Chemical Society
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• v.22 no.3
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• pp.327-329
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• 2001

• Bulletin of the Korean Chemical Society
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• v.31 no.3
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• pp.563-569
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• 2010

A new synthetic method of 2,5-disubstituted pyrrolidines is developed by the cyclization of unsaturated N-benzoyloxysulfonamides by $(CuOTf)_2{\cdot}C_6H_6$ in refluxing dichloroethane. Various N-4- and N-5-alkenyl and alkynyl N-benzoyloxysulfonamides are cyclized to give pyrrolidines. The cyclization proceeds via addition of sulfonamidoyl radicals to intramolecular unsaturated bonds or allylic hydrogen abstraction with the radical intermediates.

• Bulletin of the Korean Chemical Society
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• v.28 no.10
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• pp.1844-1846
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• 2007

• Bulletin of the Korean Chemical Society
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• v.20 no.6
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• pp.633-635
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• 1999

• YAKHAK HOEJI
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• v.40 no.3
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• pp.300-305
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• 1996

The base-induced elimination of N-protected 2-(bromomethyl)pyrrolidines 12a-c with KHMDS in THF at -78$^{\circ}C$ for 1h gave exocyclic enamines 13a-c. The acidic catalyzed pr otonation on ${\beta}$-carbon atom of 2-(methylene)pyrrolidines 13a-c with $H_3PO_4$ formed endocyclic N-iminium intermediates 14(or 15). Nucleophilic attack of alpha-carbon atom and hydrolysis of N-iminium ion gave carbocationic adduct (aminoalcohol) 16 from which 5-amino-2-pentanones 17a-c were formed after deprotonation.

• Journal of the Korean Chemical Society
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• v.45 no.6
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• pp.549-554
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• 2001

For the development of new COX-2 inhibitor, novel compound were synthesized through induction an arylsulfonyl group to 1-position, an arylcarboxamidyl group to 2-position and an alkyl group to 4-position of L-proline. We started from 4-hydroxy-L-proline, the 4-methylphenylsulfonyl of 1-position was introduced through N-tosylation and the carboxylic acid group was protected by esterification. We sucessfully converted to a various derivatives 4b-d for O-alkyl-(or aralkyl)ation of 4-position using silver oxide as catalysis. The 4-alkyloxy-1-tosyl L-prolines 5b-d were synthesized through base-hydrolysis for the deprotection of carboxylic acid. Final compound 1,2,4-substituted pyrrolidines, 4-alkyloxy-2-phenylcarboxamidyl-1-tosyl pyrrolidines 6a-d were synthesized through the condensation of arylamine with 3 and 5b-d using DCC.

• Bulletin of the Korean Chemical Society
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• v.30 no.11
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• pp.2799-2802
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• 2009

• Bulletin of the Korean Chemical Society
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• v.15 no.10
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• pp.825-827
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• 1994

• Proceedings of the PSK Conference
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• 2003.10b
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• pp.178.2-178.2
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• 2003

Naturally occurring sugar mimics with a nitrogen in the ring are classified into five structural classes: polyhydroxylated pyrrolidines, piperidines, indolizidines. pyrrolizidine, and nortropanes. Glycosidase are involved in a wide range of important biological processes, such as intestinal digestion, post-translational processing of glycoproteins and the lysosomal catabolism of glycoconjugate. The realization that alkaloidal sugar mimics might have enormous therapeutic potential in many diseases such as viral infection, cancer and diabetes has led to increasing interest and demand for these compounds. (omitted)

• Proceedings of the Korean Society of Applied Pharmacology
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• 2003.11a
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• pp.115-115
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• 2003

Naturally occurring sugar mimics with a nitrogen in the ring are classified into five structural classes: polyhydroxylated pyrrolidines, piperidines, indolizidines. pyrrolizidine, and nortropanes. Glycosidase are involved in a wide range of important biological processes, such as intestinal digestion, post-translational processing of glycoproteins and the lysosomal catabolism of glycoconjugate. The realization that alkaloidal sugar mimics might have enormous therapeutic potential in many diseases such as viral infection, cancer and diabetes has led to increasing interest and demand for these compounds. Most of these effects can be shown to result from the direct or indrect inhibition of glycosidases.