A synthesis of the C1-N12 tripeptide fragment of sanglifehrin A

被引:29
作者
Bänteli, R [1 ]
Brun, I [1 ]
Hall, P [1 ]
Metternich, R [1 ]
机构
[1] Novartis Pharma AG, CH-4002 Basel, Switzerland
关键词
D O I
10.1016/S0040-4039(99)00212-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of the C-1-N-12 tripeptide of the novel immunosuppressant sanglifehrin A is described. Evans oxazolidinone methodology was used to install the C8 stereocentre of the meta-tyrosine sub-unit. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2109 / 2112
页数:4
相关论文
共 9 条
[1]   TOTAL SYNTHESIS OF (+)-CALYCULIN-A [J].
EVANS, DA ;
GAGE, JR ;
LEIGHTON, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9434-9453
[2]   CONTRASTERIC CARBOXIMIDE HYDROLYSIS WITH LITHIUM HYDROPEROXIDE [J].
EVANS, DA ;
BRITTON, TC ;
ELLMAN, JA .
TETRAHEDRON LETTERS, 1987, 28 (49) :6141-6144
[3]   THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS [J].
EVANS, DA ;
BRITTON, TC ;
ELLMAN, JA ;
DOROW, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4011-4030
[4]   AZINOTHRICIN SYNTHETIC STUDIES .1. EFFICIENT ASYMMETRIC SYNTHESES OF (3R)-PIPERAZIC AND (3S)-PIPERAZIC ACIDS [J].
HALE, KJ ;
DELISSER, VM ;
MANAVIAZAR, S .
TETRAHEDRON LETTERS, 1992, 33 (49) :7613-7616
[5]   A NEW METHOD FOR SYNTHESIS OF PEPTIDES - ACTIVATION OF CARBOXYL GROUP WITH DICYCLOHEXYLCARBODIIMIDE USING 1-HYDROXYBENZOTRIAZOLES AS ADDITIVES [J].
KONIG, W ;
GEIGER, R .
CHEMISCHE BERICHTE-RECUEIL, 1970, 103 (03) :788-&
[6]   TOTAL SYNTHESIS OF A MONOCYCLIC PEPTIDE LACTONE ANTIBIOTIC, ETAMYCIN [J].
SHEEHAN, JC ;
LEDIS, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (03) :875-879
[7]   PALLADIUM CATALYZED COUPLING OF ORGANOTIN REAGENTS WITH ORGANIC ELECTROPHILES [J].
STILLE, JK .
PURE AND APPLIED CHEMISTRY, 1985, 57 (12) :1771-1780
[8]   Elevated conformational rigidity in dipeptides incorporating piperazic acid derivatives [J].
Xi, N ;
Alemany, LB ;
Ciufolini, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (01) :80-86
[9]  
1997, Patent No. 22085