IOOC route to substituted chiral pyrrolidines. Potential glycosidase inhibitors

被引：38

作者：

Falb, E ^{[1
]}

Bechor, Y ^{[1
]}

Nudelman, A ^{[1
]}

Hassner, A ^{[1
]}

Albeck, A ^{[1
]}

Gottlieb, HE ^{[1
]}

机构：

[1] Bar Ilan Univ, Dept Chem, IL-52900 Ramat Gan, Israel

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 02期

关键词：

D O I：

10.1021/jo9815094

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Branched-chain five-membered ring aza-sugar analogues, synthesized from amino acids by an intramolecular oxime-olefin cycloaddition reaction, the IOOC route, were found to be selective glycosidase inhibitors. The derivative 2,4(S)-di(hydroxymethyl)-3(S)-aminopyrrolidine, obtained from D-serine, was about 1 order of potency more active than its enantiomer obtained from L-serine.

引用

收藏

页码：498 / 506

页数：9

相关论文

共 57 条

[1] A SIMPLE ROUTE TO THE INDOLIZIDINE ALKALOID SKELETON [J].

BARTON, DHR ;

PEREIRA, MMMA ;

TAYLOR, DK .

TETRAHEDRON LETTERS, 1994, 35 (49) :9157-9158

[2] EXPEDITIOUS SYNTHESIS OF AZASUGARS BY THE DOUBLE REDUCTIVE AMINATION OF DICARBONYL SUGARS [J].

BAXTER, EW ;

REITZ, AB .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3175-3185

[3] ASYMMETRIC-SYNTHESIS OF 3S,4R-DIHYDROXYPYRROLIDINES BY REGIOSELECTIVE AND STEREOSELECTIVE HYDROXYLATION OF 4-OXOPROLINE ENOLATE [J].

BLANCO, MJ ;

SARDINA, FJ .

TETRAHEDRON LETTERS, 1994, 35 (45) :8493-8496

[4]

BOUTELLIER M, 1995, SYNLETT, P510

[5] ENANTIOSPECIFIC SYNTHESIS OF 3-PYRROLINES - A ROUTE TO NOVEL POLYHYDROXYLATED PYRROLIDINES [J].

BURLEY, I ;

HEWSON, AT .

TETRAHEDRON LETTERS, 1994, 35 (38) :7099-7102

[6] TOTAL ASYMMETRIC SYNTHESES OF 1,5-DIDEOXY-1,5-IMINOOCTITOLS AND 1,2,6,7,8-PENTAHYDROXYINDOLIZIDINES [J].

CHEN, YW ;

VOGEL, P .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2487-2496

[7] N-METHYLAMINO ACIDS IN PEPTIDE-SYNTHESIS .5. SYNTHESIS OF N-TERT-BUTYLOXYCARBONYL, N-METHYLAMINO ACIDS BY N-METHYLATION [J].

CHEUNG, ST ;

BENOITON, NL .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (05) :906-910

[8] An asymmetric approach to pyrrolidinone and pyrrolizidinone systems by intramolecular oxime-olefin cycloaddition [J].

Chiacchio, U ;

Corsaro, A ;

Pistara, V ;

Rescifina, A ;

Romeo, G ;

Romeo, R .

TETRAHEDRON, 1996, 52 (23) :7875-7884

[9] CONSTRUCTION OF HYDROXYLATED ALKALOIDS (+/-)-MANNONOLACTAM, (+/-)-DEOXYMANNOJIRIMYCIN, AND (+/-)-PROSOPININE THROUGH AZA-ANNULATION [J].

COOK, GR ;

BEHOLZ, LG ;

STILLE, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) :3575-3584

[10] Synthesis of a novel alpha-glucoside of the powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol via enzymatic glucosylation of 5-azido-5-deoxy-D-fructopyranose [J].

Dax, K ;

Ebner, M ;

Peinsipp, R ;

Stutz, AE .

TETRAHEDRON LETTERS, 1997, 38 (02) :225-226

← 1 2 3 4 5 6 →