The enantiospecific synthesis of functionalised pipecolic acids as constrained analogues of lysine

被引：44

作者：

Murray, PJ

Starkey, ID

机构：

[1] Glaxo Wellcome-Cambridge Chem. Lab., University of Cambridge, Chemical Laboratories, Cambridge, CB2 1EW, Lensfield Road

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 11期

关键词：

D O I：

10.1016/0040-4039(96)00140-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two constrained analogues of (S)-lysine have been prepared, suitably protected for solid phase peptide synthesis, in high optical and diastereomeric purity. The key step is the alkylation of the 6-oxopipecolate derivative (6) with iodoacetonitrile.

引用

页码：1875 / 1878

页数：4

共 26 条

[1] AZA-[2,3]-WITTIG REARRANGEMENTS OF VINYLAZIRIDINES AS A NOVEL ENTRY TO INDOLIZIDINE ALKALOIDS - ENANTIOSELECTIVE TOTAL SYNTHESIS OF INDOLIZIDINE 209D [J].

AHMAN, J ;

SOMFAI, P .

TETRAHEDRON LETTERS, 1995, 36 (02) :303-306

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

ANGLE, SR ;

ARNAIZ, DO .

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

[3]

ARGAMI C, 1992, J TETRAHEDRON, V48, P431

[4] CHIRAL SYNTHESIS OF 5-HYDROXY-(L)-PIPECOLIC ACIDS FROM (L)-GLUTAMIC ACID [J].

BAILEY, PD ;

BRYANS, JS .

TETRAHEDRON LETTERS, 1988, 29 (18) :2231-2234

[5] 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

[6]

BAILEY PD, 1995, CONTEMP ORG SYNTH, P173

[7] A NOVEL ENTRY TO CARBENOID SPECIES VIA BETA-KETOSULFOXONIUM YLIDES [J].

BALDWIN, JE ;

ADLINGTON, RM ;

GODFREY, CRA ;

GOLLINS, DW ;

VAUGHAN, JG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (18) :1434-1435

[8] SYNTHESIS OF OPTICALLY PURE PIPECOLATES FROM L-ASPARAGINE - APPLICATION TO THE TOTAL SYNTHESIS OF (+)-APOVINCAMINE THROUGH AMINO-ACID DECARBONYLATION AND IMINIUM ION CYCLIZATION [J].

CHRISTIE, BD ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (08) :1239-1246

[9] SYNTHESIS OF 4-PHENYLPIPERIDINES BY TANDEM WITTIG OLEFINATION-AZA-WITTIG REARRANGEMENT OF 2-BENZOYLAZIRIDINES [J].

COLDHAM, I ;

COLLIS, AJ ;

MOULD, RJ ;

RATHMELL, RE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (21) :2739-2745

[10] RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

DUTHALER, RO .

TETRAHEDRON, 1994, 50 (06) :1539-1650

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