A STEREOSELECTIVE SYNTHESIS OF HYDROXYETHYLENE AND ERYTHRO-DIHYDROXYETHYLENE DIPEPTIDE ISOSTERES - A FACIAL SELECTIVE ANTI-ALDOL REACTION

被引：12

作者：

ROSENBERG, SH

BOYD, SA

MANTEI, RA

机构：

[1] Cardiovascular Research Division, Abbott Laboratories, Abbott Park

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 45期

关键词：

HYDROXYETHYLENE ISOSTERE; ANTI-ALDOL; ASPARTIC PROTEINASE; RENIN INHIBITOR; FACIAL SELECTIVE;

D O I：

10.1016/0040-4039(91)80205-K

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Lewis-acid catalyzed anti-aldol reaction of aldehyde 4 afforded diol 6a (95% de). Aminolysis of the corresponding beta-lactone provided erythro-dihydroxyethylene dipeptide isostere 2 while the lactone-protected hydroxyethylene dipeptide isostere 3 was obtained through selective deoxygenation and acidic deprotection.

引用

收藏

页码：6507 / 6508

页数：2

相关论文

共 15 条

[1] STEREOSELECTIVE SYNTHESES OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES [J].

BOYD, SA ;

MANTEI, RA ;

HSIAO, CN ;

BAKER, WR .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :438-442

[2]

BOYD SD, UNPUB

[3] AN EFFICIENT SYNTHESIS OF THE GAMMA-LACTONE CORRESPONDING TO A HYDROXYETHYLENE DIPEPTIDE ISOSTERE USING STEREOSELECTIVE BROMOLACTONIZATION OF A CHIRAL ACYLOXAZOLIDINONE [J].

BRADBURY, RH ;

REVILL, JM ;

RIVETT, JE ;

WATERSON, D .

TETRAHEDRON LETTERS, 1989, 30 (29) :3845-3848

[4] A STEREOCONTROLLED SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES USING NOVEL, CHIRAL AMINOALKYL EPOXIDES AND GAMMA-(AMINOALKYL) GAMMA-LACTONES [J].

EVANS, BE ;

RITTLE, KE ;

HOMNICK, CF ;

SPRINGER, JP ;

HIRSHFIELD, J ;

VEBER, DF .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) :4615-4625

[5]

GENNARI C, 1985, TETRAHEDRON LETT, P797

[6] RENIN INHIBITORS [J].

GREENLEE, WJ .

MEDICINAL RESEARCH REVIEWS, 1990, 10 (02) :173-236

[7] INHIBITION OF AMINOPEPTIDASES BY PEPTIDES CONTAINING KETOMETHYLENE AND HYDROXYETHYLENE AMIDE BOND REPLACEMENTS [J].

HARBESON, SL ;

RICH, DH .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (06) :1378-1392

[8] A VERSATILE AND STEREOCONTROLLED SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES [J].

HEROLD, P ;

DUTHALER, R ;

RIHS, G ;

ANGST, C .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (05) :1178-1185

[9] SYNTHETIC AND ENZYME-INHIBITION STUDIES OF PEPSTATIN ANALOGS CONTAINING HYDROXYETHYLENE AND KETOMETHYLENE DIPEPTIDE ISOSTERES [J].

HOLLADAY, MW ;

SALITURO, FG ;

RICH, DH .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (02) :374-383

[10] RENIN INHIBITORS CONTAINING ISOSTERIC REPLACEMENTS OF THE AMIDE BOND CONNECTING THE P3 AND P2 SITES [J].

KALTENBRONN, JS ;

HUDSPETH, JP ;

LUNNEY, EA ;

MICHNIEWICZ, BM ;

NICOLAIDES, ED ;

REPINE, JT ;

ROARK, WH ;

STIER, MA ;

TINNEY, FJ ;

WOO, PKW ;

ESSENBURG, AD .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) :838-845