A facile synthesis of 3-substituted pipecolic acids, chimeric amino acids

被引：20

作者：

Makara, GM ^{[1
]}

Marshall, GR ^{[1
]}

机构：

[1] WASHINGTON UNIV,SCH MED,DEPT MOL BIOL & PHARMACOL,ST LOUIS,MO 63110

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 29期

关键词：

D O I：

10.1016/S0040-4039(97)01128-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three protected 3-substituted pipecolic acid analogs were prepared as constrained chimeric amino acid building blocks. The concise synthetic route enables the synthesis of other derivatives with sidechain functionality of amino acids as well. (C) 1997 Elsevier Science Ltd.

引用

页码：5069 / 5072

页数：4

共 17 条

[1] An efficient route to the alpha-methyl ester of L-glutamic acid, and its conversion into cis-5-hydroxy-L-pipecolic acid [J].

Adams, DR ;

Bailey, PD ;

Collier, ID ;

Heffernan, JD ;

Stokes, S .

CHEMICAL COMMUNICATIONS, 1996, (03) :349-350

[2] STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED PIPECOLIC ACIDS [J].

ANGLE, SR ;

ARNAIZ, DO .

TETRAHEDRON LETTERS, 1989, 30 (05) :515-518

[3] HIGHLY ENANTIOSELECTIVE SYNTHESIS OF PIPECOLIC ACID-DERIVATIVES VIA AN ASYMMETRIC AZA-DIELS-ALDER REACTION [J].

BAILEY, PD ;

LONDESBROUGH, DJ ;

HANCOX, TC ;

HEFFERNAN, JD ;

HOLMES, AB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (22) :2543-2544

[4] COMPETITIVE NMDA ANTAGONISTS THAT BASE THEIR ACTIVITY ON A UNIQUE CONFORMATIONAL EFFECT [J].

CLAESSON, A ;

SWAHN, BM ;

EDVINSSON, KM ;

MOLIN, H ;

SANDBERG, M .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (10) :1247-1250

[5] Convenient preparations of racemic and enantiopure methyl 6-oxopipecolate [J].

Davies, CE ;

Heightman, TD ;

Hermitage, SA ;

Moloney, MG .

SYNTHETIC COMMUNICATIONS, 1996, 26 (04) :687-696

[6] EVALUATION AND SYNTHESIS OF AMINOHYDROXYISOXAZOLES AND PYRAZOLES AS POTENTIAL GLYCINE AGONISTS [J].

DRUMMOND, J ;

JOHNSON, G ;

NICKELL, DG ;

ORTWINE, DF ;

BRUNS, RF ;

WELBAUM, B .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (09) :2116-2128

[7] A short enantioselective synthesis of pipecolic acid [J].

FernandezGarcia, C ;

McKervey, MA .

TETRAHEDRON-ASYMMETRY, 1995, 6 (12) :2905-2906

[8] Design of MHC class II (DR4) ligands using conformationally restricted imino acids at p3 and p5 [J].

Hanson, GJ ;

Vuletich, JL ;

Bedell, LJ ;

Bono, CP ;

Howard, SC ;

Welply, JK ;

Woulfe, SL ;

Zacheis, ML .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (16) :1931-1936

[9]

HRUBY VJ, 1991, HPLC PEPTIDES PROTEI, P379

[10]

KACZMAREK K, 1994, PEPTIDES CHEM STRUCT, P687

← 1 2 →