Asymmetric synthesis of (2S,4R)-4-hydroxypipecolic acid

被引：50

作者：

Brooks, CA ^{[1
]}

Comins, DL ^{[1
]}

机构：

[1] N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 19期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

asymmetric synthesis; pyridinium salts; dihydropyridones; amino acids;

D O I：

10.1016/S0040-4039(00)00460-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

引用

页码：3551 / 3553

页数：3

共 12 条

[1]

Anderson P.C., 1996, US Patent, Patent No. [5.545.640, 5545640]

[2] Enantiopure N-acyldihydropyridones as synthetic intermediates:: Asymmetric synthesis of benzomorphans [J].

Comins, DL ;

Zhang, YM ;

Joseph, SP .

ORGANIC LETTERS, 1999, 1 (04) :657-659

[3] EFFICIENT SYNTHESIS AND RESOLUTION OF TRANS-2-(1-ARYL-1-METHYLETHYL)CYCLOHEXANOLS - PRACTICAL ALTERNATIVES TO 8-PHENYLMENTHOL [J].

COMINS, DL ;

SALVADOR, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4656-4661

[4] ASYMMETRIC-SYNTHESIS OF 2-ALKYL(ARYL)-2,3-DIHYDRO-4-PYRIDONES BY ADDITION OF GRIGNARD-REAGENTS TO CHIRAL 1-ACYL-4-METHOXYPYRIDINIUM SALTS [J].

COMINS, DL ;

JOSEPH, SP ;

GOEHRING, RR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (11) :4719-4728

[5] SUBSTITUTION OF PROLINE WITH PIPECOLIC ACID AT THE SCISSILE BOND CONVERTS A PEPTIDE SUBSTRATE OF HIV PROTEINASE INTO A SELECTIVE INHIBITOR [J].

COPELAND, TD ;

WONDRAK, EM ;

TOZSER, J ;

ROBERTS, MM ;

OROSZLAN, S .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1990, 169 (01) :310-314

[6] Structure-based design of novel, urea-containing FKBP12 inhibitors [J].

Dragovich, PS ;

Barker, JE ;

French, J ;

Imbacuan, M ;

Kalish, VJ ;

Kissinger, CR ;

Knighton, DR ;

Lewis, CT ;

Moomaw, EW ;

Parge, HE ;

Pelletier, LAK ;

Prins, TJ ;

Showalter, RE ;

Tatlock, JH ;

Tucker, KD ;

Villafranca, JE .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (09) :1872-1884

[7] Preparation of (2S,4R)-4-hydroxypipecolic acid and derivatives [J].

Gillard, J ;

Abraham, A ;

Anderson, PC ;

Beaulieu, PL ;

Bogri, T ;

Bousquet, Y ;

Grenier, L ;

Guse, I ;

Lavallee, P .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06) :2226-2231

[8] SYNTHESIS OF CIS-4-(PHOSPHONOOXY)-2-PIPERIDINECARBOXYLIC ACID, AN N-METHYL-D-ASPARTATE ANTAGONIST [J].

HAYS, SJ ;

MALONE, TC ;

JOHNSON, G .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :4084-4086

[9] Epoxide derivatives of pipecolic acid and proline are inhibitors of pipecolate oxidase [J].

Ho, B ;

Zabriskie, TM .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (07) :739-744

[10] Antiviral properties of palinavir, a potent inhibitor of the human immunodeficiency virus type 1 protease [J].

Lamarre, D ;

Croteau, G ;

Wardrop, E ;

Bourgon, L ;

Thibeault, D ;

Clouette, C ;

Vaillancourt, M ;

Cohen, E ;

Pargellis, C ;

Yoakim, C ;

Anderson, P .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1997, 41 (05) :965-971

← 1 2 →