A SHORT STEREOCONTROLLED SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES

被引：25

作者：

JONES, DM ^{[1
]}

NILSSON, B ^{[1
]}

SZELKE, M ^{[1
]}

机构：

[1] FERRING AB,S-20061 MALMO,SWEDEN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 08期

关键词：

D O I：

10.1021/jo00060a052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereocontrolled synthesis of protected hydroxyethylene dipeptide isosteres 14 and 16 is described. It provides the 2R,4S,5S epimers required for the preparation of aspartic proteinase inhibitors. The choice of a benzene ring as a precursor to the carboxylic acid function has enabled us to use the readily accessible chiral Grignard reagent 3 which reacts with the protected alpha-amino aldehyde 8 stereoselectively. Kilogram quantities of 16 have been produced by this route in a satisfactory overall yield. The combination of N- and 0-protecting groups employed facilitates the incorporation of 14 or 16 into peptide-based enzyme inhibitors.

引用

收藏

页码：2286 / 2290

页数：5

相关论文

共 37 条

[1] RESOLUTION AND CONFIGURATION OF ALPHA-SUBSTITUTED PHENYLACETIC ACIDS [J].

AARON, C ;

DULL, D ;

SCHMIEGE.JL ;

JAEGER, D ;

OHASHI, Y ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (09) :2797-&

[2] CONSIDERED AS REAGENTS AND SYNTHETIC METHODS .46. 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE(DBU) - AN EFFECTIVE BASE FOR THE INTRODUCTION OF TERT-BUTYLDIMETHYLSILYL GROUP IN ORGANIC-COMPOUNDS [J].

AIZPURUA, JM ;

PALOMO, C .

TETRAHEDRON LETTERS, 1985, 26 (04) :475-476

[3] MILD PROCEDURE FOR SOLID-PHASE PEPTIDE-SYNTHESIS - USE OF "FLUORENYLMETHOXYCARBONYLAMINO-ACIDS [J].

ATHERTON, E ;

FOX, H ;

HARKISS, D ;

LOGAN, CJ ;

SHEPPARD, RC ;

WILLIAMS, BJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (13) :537-539

[4] RENIN INHIBITORS - SYNTHESES OF SUBNANOMOLAR, COMPETITIVE, TRANSITION-STATE ANALOG INHIBITORS CONTAINING A NOVEL ANALOG OF STATINE [J].

BOGER, J ;

PAYNE, LS ;

PERLOW, DS ;

LOHR, NS ;

POE, M ;

BLAINE, EH ;

ULM, EH ;

SCHORN, TW ;

LAMONT, BI ;

LIN, TY ;

KAWAI, M ;

RICH, DH ;

VEBER, DF .

JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (12) :1779-1790

[5] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[6] 9-FLUORENYLMETHOXYCARBONYL AMINO-PROTECTING GROUP [J].

CARPINO, LA ;

HAN, GY .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (22) :3404-&

[7] A HIGHLY EFFECTIVE LIGAND-BOUND RUTHENIUM CATALYST FOR CHEMOSELECTIVE DEGRADATION OF AROMATIC RINGS TO CARBOXYLIC-ACIDS [J].

CHAKRABORTI, AK ;

GHATAK, UR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2605-2609

[8] STUDIES WITH TRIALKYLSILYLTRIFLATES - NEW SYNTHESES AND APPLICATIONS [J].

COREY, EJ ;

CHO, H ;

RUCKER, C ;

HUA, DH .

TETRAHEDRON LETTERS, 1981, 22 (36) :3455-3458

[9] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].

COREY, EJ ;

VENKATESWARLU, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+

[10] A STEREOSELECTIVE METHOD FOR THE PREPARATION OF HIV-1 PROTEASE INHIBITORS BASED ON THE LEWIS ACID MEDIATED REACTION OF ALLYLSILANES AND N-BOC-ALPHA-AMINO ALDEHYDES [J].

DANIELLO, F ;

TADDEI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (19) :5247-5250

← 1 2 3 4 →