CYCLIC DIPEPTIDES - A STEREOCONTROLLED SYNTHESIS OF (2S,3R,6R) AND (2R,3R,6R)-6-TERT-BUTOXYCARBONYLAMINO-3-METHOXYCARBONYL-2-METHYL-5-OXOPERHYDRO-1,4-THIAZEPINE

被引:8
作者
CORELLI, F [1 ]
CRESCENZA, A [1 ]
DEI, D [1 ]
TADDEI, M [1 ]
BOTTA, M [1 ]
机构
[1] DIPARTIMENTO CHIM U SCHIFF,I-50121 FLORENCE,ITALY
关键词
D O I
10.1016/0957-4166(94)80115-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A stereselective synthesis of the title compounds, starting from commercially available amino acids, is described. The absolute stereochemistry of 3a and 3b has been deduced on the basis of H-1 NMR and chemical degradation studies. The formation of only these two isomers has been rationalized in terms of molecular mechanics calculations.
引用
收藏
页码:1469 / 1472
页数:4
相关论文
共 6 条
[1]   THE SYNTHESIS OF 6-AMINO-5-OXO-7-PHENYL-1,4-OXAZEPINES AS CONFORMATIONALLY CONSTRAINED GAUCHE (-) DIPEPTIDE MIMETICS [J].
BURKHOLDER, TP ;
HUBER, EW ;
FLYNN, GA .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (02) :231-234
[2]  
GAROFALO A, 1990, HETEROCYCLES, V31, P1291
[3]   THIOANALOGS OF ANTITUMOR ANTIBIOTICS .2. SYNTHESIS AND PRELIMINARY INVITRO CYTOTOXICITY EVALUATION OF TRICYCLIC [1,4]BENZOTHIAZEPINE DERIVATIVES [J].
GAROFALO, A ;
BALCONI, G ;
BOTTA, M ;
CORELLI, F ;
DINCALCI, M ;
FABRIZI, G ;
FIORINI, I ;
LAMBA, D ;
NACCI, V .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (03) :213-220
[4]  
ITO S, 1993, CHEM PHARM BULL, V41, P1066
[5]  
WIELAND T, 1962, LIEBIGS ANN CHEM, V658, P181
[6]   N-TERT.-BUTYLOXYCARBONYL-L-CYSTEINE AND S-SUBSTITUTED DERIVATIVES [J].
ZAHN, H ;
HAMMERST.K .
CHEMISCHE BERICHTE-RECUEIL, 1969, 102 (03) :1048-&