ASYMMETRIC-SYNTHESIS OF A NOVEL PHENYLOGOUS AMINO-ACID MIMICKING AN EXTENDED DIPEPTIDE

被引：19

作者：

CHEN, L

TRILLES, RV

TILLEY, JW

机构：

[1] Roche Research Center, Hoffmann-La Roche Inc., Nutley, New Jersey

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 48期

关键词：

D O I：

10.1016/0040-4039(95)01877-K

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of an orthogonally protected form of phenylogous amino acid I which mimics an extended conformation of the dipeptide Arg-Gly was achieved. Key steps involve a diastereoselective addition of allylic organometallic reagents to chiral imine 2 and a palladium mediated carboalkoxylation of aryl bromide 5.

引用

收藏

页码：8715 / 8718

页数：4

相关论文

共 26 条

[1] ENANTIOSELECTIVE SYNTHESIS OF HOMOALLYLIC AMINES BY ADDITION OF ALLYLMETAL REAGENTS TO IMINES DERIVED FROM (S)-VALINE ESTERS [J].

BASILE, T ;

BOCOUM, A ;

SAVOIA, D ;

UMANIRONCHI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7766-7773

[2] UNRAVELING THE STRUCTURE OF IL-2 [J].

BAZAN, JF .

SCIENCE, 1992, 257 (5068) :410-412

[3] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[4]

DAVIES SG, 1989, HETEROCYCLES, V28, P163

[5] ORGANOCERIUM ADDITIONS TO SAMP-HYDRAZONES - GENERAL-SYNTHESIS OF CHIRAL AMINES [J].

DENMARK, SE ;

WEBER, T ;

PIOTROWSKI, DW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (07) :2224-2225

[6]

DODD DS, 1994, TETRAHEDRON LETT, V50, P977

[7] DIASTEREOSELECTIVE SYNTHESIS OF CHIRAL SECONDARY-AMINES WITH 2 CHIRAL CENTERS DIRECTLY ATTACHED TO THE NITROGEN ATOM [J].

ELEVELD, MB ;

HOGEVEEN, H ;

SCHUDDE, EP .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3635-3642

[8] PEPTIDOMIMETICS FOR RECEPTOR LIGANDS DISCOVERY, DEVELOPMENT, AND MEDICAL PERSPECTIVES [J].

GIANNIS, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (09) :1244-1267

[9] SYNTHETIC APPROACHES TO THE AZOLE PEPTIDE MIMETICS [J].

GORDON, TD ;

SINGH, J ;

HANSEN, PE ;

MORGAN, BA .

TETRAHEDRON LETTERS, 1993, 34 (12) :1901-1904

[10] VINYLOGOUS POLYPEPTIDES - AN ALTERNATIVE PEPTIDE BACKBONE [J].

HAGIHARA, M ;

ANTHONY, NJ ;

STOUT, TJ ;

CLARDY, J ;

SCHREIBER, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (16) :6568-6570