Synthesis of 2-fluoro- and 6-fluoro-(2S,3R)-(3,4-dihydroxyphenyl) serine as potential in vivo precursors of fluorinated norepinephrines

被引：23

作者：

Herbert, B ^{[1
]}

Kim, IH ^{[1
]}

Kirk, KL ^{[1
]}

机构：

[1] NIDDKD, Bioorgan Chem Lab, NIH, Bethesda, MD 20892 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 14期

关键词：

D O I：

10.1021/jo010327y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compounds were prepared by the aldol condensation of 3,4-dibenzyloxy-2-fluorobenzaldehyde and 4,5-dibenzyloxy-2-fluorobenzaldehyde with the oxazolidinone 2, a chiral glycine equivalent. Removal of the chiral auxiliary and blocking groups produced the target amino acids 2-fluoro- and 6-fluoro-(2S,3R)-(3,4-dihydroxyphenyl)serine (1b and 1c) in > 98% ee.

引用

页码：4892 / 4897

页数：6

共 19 条

[1] SYNTHESES AND ADRENERGIC ACTIVITIES OF RING-FLUORINATED EPINEPHRINES [J].

ADEJARE, A ;

GUSOVSKY, F ;

PADGETT, W ;

CREVELING, CR ;

DALY, JW ;

KIRK, KL .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (10) :1972-1977

[2] PRESSOR EFFECT OF L-THREO-3,4-DIHYDROXYPHENYLSERINE IN RATS [J].

ARAKI, H ;

TANAKA, C ;

FUJIWARA, H ;

NAKAMURA, M ;

OHMURA, I .

JOURNAL OF PHARMACY AND PHARMACOLOGY, 1981, 33 (12) :772-777

[3] SYNTHESIS OF 2-FLUORO AND 6-FLUORO ANALOGS OF THREO-3-(3,4-DIHYDROXYPHENYL) SERINE (2-FLUORO-THREO-DOPS AND 6-FLUORO-THREO-DOPS) [J].

CHEN, BH ;

NIE, JY ;

SINGH, M ;

PIKE, VW ;

KIRK, KL .

JOURNAL OF FLUORINE CHEMISTRY, 1995, 75 (01) :93-101

[4] BIFUNCTIONAL CHIRAL AUXILIARIES .2. THE SYNTHESIS OF 1,3-DIACYLIMIDAZOLIDIN-2-ONES FROM 1,2-DIAMINES [J].

DAVIES, SG ;

MORTLOCK, AA .

TETRAHEDRON LETTERS, 1991, 32 (36) :4791-4794

[5] ASYMMETRIC GLYCINE ENOLATE ALDOL REACTIONS - SYNTHESIS OF CYCLOSPORINES UNUSUAL AMINO-ACID, MEBMT [J].

EVANS, DA ;

WEBER, AE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (21) :6757-6761

[6] The treatment of neurogenic orthostatic hypotension with 3,4-DL-threo-dihydroxyphenylserine - A randomized, placebo-controlled, crossover trial [J].

Freeman, R ;

Landsberg, L ;

Young, J .

NEUROLOGY, 1999, 53 (09) :2151-2157

[7] AN IMPROVED SYNTHESIS OF 4-FLUOROVERATROLE - EFFICIENT ROUTE TO 6-FLUOROVERATRALDEHYDE AND 6-FLUORO-D,L-DOPA [J].

FURLANO, DC ;

KIRK, KL .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (21) :4073-4075

[8] SELECTIVE REMOVAL OF AN N-BOC PROTECTING GROUP IN THE PRESENCE OF A TERT-BUTYL ESTER AND OTHER ACID-SENSITIVE GROUPS [J].

GIBSON, FS ;

BERGMEIER, SC ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3216-3218

[9] ENZYMATIC OXIDATIVE CONVERSION OF THIO TO OXO BY BAKERS-YEAST IN THIOCARBAMATES AND THIOUREAS [J].

KAMAL, A ;

RAO, MV ;

RAO, AB .

CHEMISTRY LETTERS, 1990, (04) :655-656

[10] Increasing CNS norepinephrine levels by the precursor L-DOPS facilitate beam-walking recovery after sensorimotor cortex ablation in rats [J].

Kikuchi, K ;

Nishino, K ;

Ohyu, H .

BRAIN RESEARCH, 2000, 860 (1-2) :130-135

← 1 2 →