Convenient syntheses of 2-, 5- and 6-fluoro- and 2,6-difluoro-L-DOPA

被引:14
作者
Deng, WP [1 ]
Wong, KA [1 ]
Kirk, KL [1 ]
机构
[1] NIDDKD, Bioorgan Chem Lab, NIH, Bethesda, MD 20892 USA
关键词
D O I
10.1016/S0957-4166(02)00321-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Alkylation under phase transfer conditions of the chiral glycine synthon 2 (prepared from the commercially available Oppolzer chiral sultam) with fluorinated analogues of 3,4-dimethoxybenzyl chloride proceeded with high diastereoselectivity. Hydrolysis of the Schiff base, removal of the chiral auxiliary and HBr demethylation produced 2-, 5-, 6-fluoro- and 2,6-difluoro-L-DOPA in e.e. of >99%. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1135 / 1140
页数:6
相关论文
共 30 条
[11]  
FIRNAU G, 1986, APPL RADIAT ISOTOPES, V37, P669
[12]   CEREBRAL METABOLISM OF 6-[F-18]FLUORO-L-3,4-DIHYDROXYPHENYLALANINE IN THE PRIMATE [J].
FIRNAU, G ;
SOOD, S ;
CHIRAKAL, R ;
NAHMIAS, C ;
GARNETT, ES .
JOURNAL OF NEUROCHEMISTRY, 1987, 48 (04) :1077-1082
[13]   AROMATIC FLUORINATION WITH XENON DIFLUORIDE - L-3,4-DIHYDROXY-6-FLUORO-PHENYLALANINE [J].
FIRNAU, G ;
CHIRAKAL, R ;
SOOD, S ;
GARNETT, S .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1980, 58 (14) :1449-1450
[14]   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
[15]   NO-CARRIER-ADDED (NCA) SYNTHESIS OF 6-[F-18]FLUORO-L-DOPA USING 3,5,6,7,8,8A-HEXAHYDRO-7,7,8A-TRIMETHYL-[6S-(6-ALPHA, 8-ALPHA, 8-ALPHA-BETA)]-6,8-METHANO-2 H-1,4-BENZOXAZIN-2-ONE [J].
HORTI, A ;
REDMOND, DE ;
SOUFER, R .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1995, 36 (05) :409-423
[16]   ASYMMETRIC-SYNTHESIS OF L-DIPHENYLALANINE AND L-9-FLUORENYLGLYCINE VIA ROOM-TEMPERATURE ALKYLATIONS OF A SULTAM-DERIVED GLYCINE IMINE [J].
JOSIEN, H ;
MARTIN, A ;
CHASSAING, G .
TETRAHEDRON LETTERS, 1991, 32 (45) :6547-6550
[17]   2-SUBSTITUTED DERIVATIVES OF 3,4-DIHYDROXYPHENYLALANINE [J].
KAISER, C ;
BURGER, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (16) :4365-4370
[18]   SYNTHESIS AND BIOLOGICAL PROPERTIES OF 2-FLUORONOREPINEPHRINES, 5-FLUORONOREPINEPHRINES, AND 6-FLUORONOREPINEPHRINES [J].
KIRK, KL ;
CANTACUZENE, D ;
NIMITKITPAISAN, Y ;
MCCULLOH, D ;
PADGETT, WL ;
DALY, JW ;
CREVELING, CR .
JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (12) :1493-1497
[19]   IMPROVED SYNTHESIS OF FLUOROVERATROLES AND FLUOROPHENETHYLAMINES VIA ORGANO-LITHIUM REAGENTS [J].
LADD, DL ;
WEINSTOCK, J .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (01) :203-206
[20]  
LEMAIRE C, 1998, J LABELLED CPD RA S1, V42, pS113