MODIFICATION OF MACROLIDE ANTIBIOTICS - SYNTHESIS OF 11-DEOXY-11-(CARBOXYAMINO)-6-O-METHYLERYTHROMYCIN-A 11,12-(CYCLIC ESTERS) VIA AN INTRAMOLECULAR MICHAEL REACTION OF O-CARBAMATES WITH AN ALPHA,BETA-UNSATURATED KETONE

被引:82
作者
BAKER, WR
CLARK, JD
STEPHENS, RL
KIM, KH
机构
关键词
D O I
10.1021/jo00245a038
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
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页码:2340 / 2345
页数:6
相关论文
共 15 条
[1]   ANTIBACTERIAL ACTIVITY OF ROXITHROMYCIN - A LABORATORY EVALUATION [J].
CHANTOT, JF ;
BRYSKIER, A ;
GASC, JC .
JOURNAL OF ANTIBIOTICS, 1986, 39 (05) :660-668
[2]   ERYTHROMYCIN SERIES .11. RING EXPANSION F ERYTHROMYCIN-A OXIME BY THE BECKMANN REARRANGEMENT [J].
DJOKIC, S ;
KOBREHEL, G ;
LAZAREVSKI, G ;
LOPOTAR, N ;
TAMBURASEV, Z ;
KAMENAR, B ;
NAGL, A ;
VICKOVIC, I .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (11) :1881-1890
[3]  
DJOKIC S, 1966, TETRAHEDRON LETT, P1645
[4]   CONFIGURATION OF 9-IMINO DERIVATIVES OF ERYTHROMYCIN [J].
EGAN, RS ;
FREIBERG, LA ;
WASHBURN, WH .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (17) :2492-2494
[5]   REACTIONS WITH N-CARBONYLSULFAMOYL CHLORIDE [J].
GRAF, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1968, 7 (03) :172-&
[6]  
HAUSKE JR, 1982, J ORG CHEM, V47, P1595, DOI 10.1021/jo00347a052
[7]   CARBAMATE-MEDIATED FUNCTIONALIZATION OF UNSATURATED ALCOHOLS .3. INTRAMOLECULAR MICHAEL ADDITION OF O-CARBAMATES TO ALPHA,BETA-UNSATURATED ESTERS - A NEW DIASTEREOSELECTIVE AMINATION IN AN ACYCLIC SYSTEM [J].
HIRAMA, M ;
SHIGEMOTO, T ;
YAMAZAKI, Y ;
ITO, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (06) :1797-1798
[8]   THE TOXICITY OF METABOLITES OF SODIUM VALPROATE IN CULTURED-HEPATOCYTES [J].
KINGSLEY, E ;
GRAY, P ;
TOLMAN, KG ;
TWEEDALE, R .
JOURNAL OF CLINICAL PHARMACOLOGY, 1983, 23 (04) :178-185
[9]   ACID DEGRADATION OF ERYTHROMYCIN-A AND ERYTHROMYCIN-B [J].
KURATH, P ;
JONES, PH ;
EGAN, RS ;
PERUN, TJ .
EXPERIENTIA, 1971, 27 (04) :362-&
[10]  
MANNISOT PT, 1983, INT C CHEMOTHER, V5, P107