Synthesis of β-hydroxy-β-(fluoronitrophenyl)alanines:: Vital components in the assembly of biologically active cyclic peptides

被引:14
作者
Hutton, CA [1 ]
机构
[1] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia
关键词
D O I
10.1021/ol9906054
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Numerous biologically active cyclic peptides, such as the antibiotic vancomycin, contain amino acid residues connected through side-chain biaryl or aryl-alkyl ether linkages. Nucleophilic aromatic substitution reactions have recently been shown to provide a general method for the formation of such ether linkages, and consequently the synthesis of functionalized fluoronitro-substituted aromatic amino acids is of great interest. Herein, a method for the stereospecific synthesis of 3-fluoro-4-nitro- and 4-fluoro-3-nitro-threo-beta-hydroxyphenylalanine described.
引用
收藏
页码:295 / 297
页数:3
相关论文
共 23 条
[1]   SNAR-BASED MACROCYCLIZATION - AN APPLICATION TO THE SYNTHESIS OF VANCOMYCIN FAMILY MODELS [J].
BEUGELMANS, R ;
SINGH, GP ;
BOISCHOUSSY, M ;
CHASTANET, J ;
ZHU, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5535-5542
[2]  
BEUGELMANS R, 1994, TETRAHEDRON LETT, V35, P7741
[3]   A formal total synthesis of deoxybouvardin [J].
Bigot, A ;
Beugelmans, R ;
Zhu, JP .
TETRAHEDRON, 1997, 53 (31) :10753-10764
[4]   Synthesis of the vancomycin CDE ring system [J].
Boger, DL ;
Beresis, RT ;
Loiseleur, O ;
Wu, JH ;
Castle, SL .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (07) :721-724
[5]   AN UNUSUALLY FACILE SNAR 14-MEMBERED BIARYL ETHER MACROCYCLIZATION REACTION SUITABLE FOR PREPARATION OF THE CYCLOISODITYROSINE SUBUNIT OF BOUVARDIN, DEOXYBOUVARDIN AND RELATED AGENTS [J].
BOGER, DL ;
BORZILLERI, RM .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (11) :1187-1190
[6]   Synthesis of the vancomycin CD and DE ring systems [J].
Boger, DL ;
Borzilleri, RM ;
Nukui, S ;
Beresis, RT .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) :4721-4736
[7]   Total synthesis of the cyclopeptide alkaloid sanjoinine G1 and its C-11 epimer [J].
East, SP ;
Shao, F ;
Williams, L ;
Joullie, MM .
TETRAHEDRON, 1998, 54 (44) :13371-13390
[8]   Neighbouring group effects promote substitution reactions over elimination and provide a stereocontrolled route to chloramphenicol [J].
Easton, CJ ;
Hutton, CA ;
Merrett, MC ;
Tiekink, ERT .
TETRAHEDRON, 1996, 52 (20) :7025-7036
[9]   STEREOCONTROLLED SYNTHESIS OF BETA-HYDROXYPHENYLALANINE AND BETA-HYDROXYTYROSINE DERIVATIVES [J].
EASTON, CJ ;
HUTTON, CA ;
ROSELT, PD ;
TIEKINK, ERT .
TETRAHEDRON, 1994, 50 (24) :7327-7340
[10]   Synthesis of the orienticin C M(2-4) macrocycle utilizing a nucleophilic aromatic substitution strategy [J].
Evans, DA ;
Watson, PS .
TETRAHEDRON LETTERS, 1996, 37 (19) :3251-3254