Highly stereoselective synthesis of anti-N-protected-α-amino epoxides

被引：44

作者：

Hoffman, RV ^{[1
]}

Weiner, WS ^{[1
]}

Maslouh, N ^{[1
]}

机构：

[1] New Mexico State Univ, Dept Chem & Biochem, Las Cruces, NM 88003 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 17期

关键词：

D O I：

10.1021/jo010319h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient method for the synthesis of anti-N-protected amino epoxides from carbamate-protected amino acids is described. The two key steps are the monobromination of a beta -ketoester and chelation-controlled reduction of a bromomethyl ketone intermediate. Good overall yields, high diastereoselectivity, and excellent functional group compatibility are characteristic.

引用

页码：5790 / 5795

页数：6

共 31 条

[1] STEREOCONTROLLED SYNTHESIS OF ERYTHRO N-PROTECTED ALPHA-AMINO EPOXIDES AND PEPTIDYL EPOXIDES [J].

ALBECK, A ;

PERSKY, R .

TETRAHEDRON, 1994, 50 (21) :6333-6346

[2] IMPROVED STEREOCONTROLLED SYNTHESIS OF THREO PEPTIDYL EPOXIDES [J].

ALBECK, A ;

PERSKY, R .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (03) :653-657

[3]

Albeck A, 2000, DRUG DEVELOP RES, V50, P425, DOI 10.1002/1098-2299(200007/08)50:3/4<425::AID-DDR25>3.0.CO

[4]

2-B

[5] RENIN INHIBITORS CONTAINING C-TERMINI DERIVED FROM MERCAPTOHETEROCYCLES [J].

ASHTON, WT ;

CANTONE, CL ;

MEURER, LC ;

TOLMAN, RL ;

GREENLEE, WJ ;

PATCHETT, AA ;

LYNCH, RJ ;

SCHORN, TW ;

STROUSE, JF ;

SIEGL, PKS .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (11) :2103-2112

[6] HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF THREO OR ERYTHRO AMINOALKYL EPOXIDES FROM ALPHA-AMINO-ACIDS [J].

BARLUENGA, J ;

BARAGANA, B ;

CONCELLON, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6696-6699

[7] THE CONVERSION OF ALPHA-BROMO-BETA-DICARBONYLS TO VICINAL TRICARBONYLS USING DIMETHYLDIOXIRANE AND BASE [J].

COATS, SJ ;

WASSERMAN, HH .

TETRAHEDRON LETTERS, 1995, 36 (42) :7735-7738

[8] INHIBITION OF AMINOPEPTIDASES BY PEPTIDES CONTAINING KETOMETHYLENE AND HYDROXYETHYLENE AMIDE BOND REPLACEMENTS [J].

HARBESON, SL ;

RICH, DH .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (06) :1378-1392

[9] SYNTHETIC STUDIES OF DIDEMNINS .3. SYNTHESES OF STATINE AND ISOSTATINE STEREOISOMERS [J].

HARRIS, BD ;

JOULLIE, MM .

TETRAHEDRON, 1988, 44 (12) :3489-3500

[10] SYNTHESIS OF N-PROTECTED ERYTHRO-PHENYLALANYLEPOXIDES [J].

HEINSOO, A ;

RAIDARU, G ;

LINASK, K ;

JARV, J ;

ZETTERSTROM, M ;

LANGEL, U .

TETRAHEDRON-ASYMMETRY, 1995, 6 (09) :2245-2247

← 1 2 3 4 →