NEW CLASS OF ANTI-TUMOR COMPOUNDS - 5'-NOR AND 5',6'-SECO DERIVATIVES OF VINBLASTINE-TYPE ALKALOIDS

被引:73
作者
MANGENEY, P [1 ]
ANDRIAMIALISOA, RZ [1 ]
LANGLOIS, N [1 ]
LANGLOIS, Y [1 ]
POTIER, P [1 ]
机构
[1] CNRS,INST CHIM SUBST NAT,F-91190 GIF SUR YVETTE,FRANCE
关键词
D O I
10.1021/jo01336a006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction medium obtained after applying the modified Polonovski reaction to the Nb'-oxide of anhydrovinblastine (3) led mainly to seco C5'-C6' derivatives after treatment with various nucleophiles. In the presence of cyanide ion, a minor product formed by nucleophilic attack onto the conjugated immonium salt 7 was also isolated. On the other hand, 20'-deoxyleurosidine Nb'-oxide (20) led only to seco C5'-C6' derivatives. © 1979, American Chemical Society. All rights reserved.
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页码:3765 / 3768
页数:4
相关论文
共 14 条
[1]  
Basha A., 1976, TETRAHEDRON LETT, P2351
[2]  
BROWN RT, 1978, TETRAHEDRON LETT, P4251
[3]  
GIZZI LR, 1969, TETRAHEDRON LETT, P3117
[4]   VERSATILE AND INEXPENSIVE ELECTRONIC SYSTEM FOR A HIGH-RESOLUTION NMR SPECTROMETER [J].
KAN, S ;
GONORD, P ;
DURET, C ;
SALSET, J ;
VIBET, C .
REVIEW OF SCIENTIFIC INSTRUMENTS, 1973, 44 (12) :1725-1733
[5]  
KUTNEY JP, 1976, HETEROCYCLES, V4, P997
[6]   ANTITUMOUR ALKALOIDS OF VINBLASTINE-TYPE - IS LEUROSINE AN ARTIFACT [J].
LANGLOIS, N ;
POTIER, P .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (03) :102-103
[7]   APPLICATION OF A MODIFICATION OF POLONOVSKI REACTION TO SYNTHESIS OF VINBLASTINE-TYPE ALKALOIDS [J].
LANGLOIS, N ;
GUERITTE, F ;
LANGLOIS, Y ;
POTIER, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (22) :7017-7024
[8]  
LANGLOIS N, 1976, TETRAHEDRON LETT, P1099
[9]  
LANGLOIS Y, 1976, TETRAHEDRON LETT, P3945
[10]  
MANGENEY P, J AM CHEM SOC