A short, efficient synthesis of monofluoro ketomethylene peptide isostere core units

被引：12

作者：

Hoffman, RV

Saenz, JE

机构：

[1] Dept. of Chemistry and Biochemistry, New Mexico State University, Las Cruces

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 49期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(97)10282-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Monofluoro ketomethylene peptide isosteres can be prepared by a four step sequence from carboxylic acids in satisfactory overall yields (30-60%). Fluorine is introduced by electrophilic fluorination of a beta-ketoester enolate with SelectFluor(TM). (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：8469 / 8472

页数：4

相关论文

共 16 条

[1] SYNTHESIS OF THE KETODIFLUOROMETHYLENE DIPEPTIDE ISOSTERE [J].

DAMON, DB ;

HOOVER, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) :6439-6442

[2] DESIGN, SYNTHESIS, AND KINETIC EVALUATION OF A UNIQUE CLASS OF ELASTASE INHIBITORS, THE PEPTIDYL ALPHA-KETOBENZOXAZOLES, AND THE X-RAY CRYSTAL-STRUCTURE OF THE COVALENT COMPLEX BETWEEN PORCINE PANCREATIC ELASTASE AND AC-ALA-PRO-VAL-2-BENZOXAZOLE [J].

EDWARDS, PD ;

MEYER, EF ;

VIJAYALAKSHMI, J ;

TUTHILL, PA ;

ANDISIK, DA ;

GOMES, B ;

STRIMPLER, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1854-1863

[3] FLUORO KETONE CONTAINING PEPTIDES AS INHIBITORS OF HUMAN RENIN [J].

FEARON, K ;

SPALTENSTEIN, A ;

HOPKINS, PB ;

GELB, MH .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (09) :1617-1622

[4] SYNTHESIS OF THE MONOFLUORO KETONE PEPTIDE ISOSTERE [J].

GARRETT, GS ;

EMGE, TJ ;

LEE, SC ;

FISCHER, EM ;

DYEHOUSE, K ;

MCIVER, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (16) :4823-4826

[5] FLUORO KETONE INHIBITORS OF HYDROLYTIC ENZYMES [J].

GELB, MH ;

SVAREN, JP ;

ABELES, RH .

BIOCHEMISTRY, 1985, 24 (08) :1813-1817

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

HARRIS, BD ;

JOULLIE, MM .

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

[7] A short, enantiospecific synthesis of a protected seco acid precursor to (R,R)-(-)-pyrenophorin [J].

Hoffman, RV ;

Patonay, T ;

Nayyar, NK ;

Tao, JH .

TETRAHEDRON LETTERS, 1996, 37 (14) :2381-2384

[8] A SIMPLE SYNTHETIC APPROACH TO CBZ-PHE-PSI-(CH2)GLY-PRO-OME AND RELATED PEPTIDE ISOSTERES [J].

HOFFMAN, RV ;

KIM, HO .

TETRAHEDRON LETTERS, 1992, 33 (25) :3579-3582

[9] SYNTHESIS AND N-TERMINAL AND C-TERMINAL EXTENSION OF PEPTIDYL ALPHA,ALPHA-DIFLUOROALKYL KETONES [J].

HONG, WP ;

DONG, LW ;

CAI, ZH ;

TITMAS, R .

TETRAHEDRON LETTERS, 1992, 33 (06) :741-744

[10] INHIBITION OF SERINE PROTEASES BY PEPTIDYL FLUOROMETHYL KETONES [J].

IMPERIALI, B ;

ABELES, RH .

BIOCHEMISTRY, 1986, 25 (13) :3760-3767