A stereocontrolled synthesis of monofluoro ketomethylene dipeptide isosteres

被引：15

作者：

Hoffman, RV ^{[1
]}

Tao, JH ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 24期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(98)00783-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple, stereocontrolled synthesis of monofluoro ketomethylene dipeptide isosteres has been developed. The method is short (6 steps) and diastereoselective (85-95% de) and enantioselective (>95% ee). (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4195 / 4198

页数：4

共 33 条

[1] ENZYME-INHIBITORS - GROUND-STATE TRANSITION-STATE ANALOGS [J].

ABELES, RH .

DRUG DEVELOPMENT RESEARCH, 1987, 10 (04) :221-234

[2] A diastereoselective synthesis of (2S, 3R, 4S)-2-amino-1-cyclohexyl-6-methylheptane-3,4-diol, the Abbott aminodiol. [J].

Alexander, CW ;

Liotta, DC .

TETRAHEDRON LETTERS, 1996, 37 (12) :1961-1964

[3] EFFICIENT PREPARATION OF PEPTIDYL PENTAFLUOROETHYL KETONES [J].

ANGELASTRO, MR ;

BURKHART, JP ;

BEY, P ;

PEET, NP .

TETRAHEDRON LETTERS, 1992, 33 (23) :3265-3268

[4]

[Anonymous], 1991, Fluorine in Bioorganic Chemistry

[5] EFFICIENT ONE-POT SYNTHESIS OF N-TRITYL AMINO-ACIDS [J].

BARLOS, K ;

PAPAIOANNOU, D ;

THEODOROPOULOS, D .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07) :1324-1326

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

DAMON, DB ;

HOOVER, DJ .

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

[7] SELECTIVE, ELECTROPHILIC FLUORINATIONS USING N-FLUORO-O-BENZENEDISULFONIMIDE [J].

DAVIS, FA ;

HAN, W ;

MURPHY, CK .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4730-4737

[8] Nonpeptidic inhibitors of human neutrophil elastase .7. Design, synthesis, and in vitro activity of a series of pyridopyrimidine trifluoromethyl ketones [J].

Edwards, PD ;

Andisik, DW ;

Strimpler, AM ;

Gomes, B ;

Tuthill, PA .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (05) :1112-1124

[9] Regio- and enantioselective synthesis of alpha-fluoroketones by electrophilic fluorination of alpha-silylketone enolates with N-fluorobenzosulfonimide [J].

Enders, D ;

Potthoff, M ;

Raabe, G ;

Runsink, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (21) :2362-2364

[10] 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

← 1 2 3 4 →