CYCLOADDITION REACTIONS OF CARBOHYDRATE-DERIVATIVES .3. A NEW ROUTE TO SWAINSONINE ANALOGS

被引:27
作者
HERCZEGH, P
KOVACS, I
SZILAGYI, L
ZSELY, M
SZTARICSKAI, F
BERECIBAR, A
OLESKER, A
LUKACS, G
机构
[1] LAJOS KOSSUTH UNIV,DEPT ORGAN CHEM,H-4010 DEBRECEN,HUNGARY
[2] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE
关键词
D O I
10.1016/S0040-4039(00)79832-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Swainsonine analogs 10 and 12 have been synthesized from D- and L-arabinose, respectively, using cyclocondensation of azomethines with Danishefsky's diene followed by stereoselective carbonyl and double bond reduction of the resulting pyridones, chain shortening and ring closure by reductive amination.
引用
收藏
页码:3133 / 3136
页数:4
相关论文
共 13 条
[1]   SPECTROSCOPIC INVESTIGATION OF SWAINSONINE - ALPHA-MANNOSIDASE INHIBITOR ISOLATED FROM SWAINSONA-CANESCENS [J].
COLEGATE, SM ;
DORLING, PR ;
HUXTABLE, CR .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (10) :2257-2264
[2]  
HERCZEGH P, 1989, HETEROCYCLES, V28, P887
[3]   STUDIES OF AN IMMUNOMODULATOR, SWAINSONINE .1. ENHANCEMENT OF IMMUNE-RESPONSE BY SWAINSONINE INVITRO [J].
HINO, M ;
NAKAYAMA, O ;
TSURUMI, Y ;
ADACHI, K ;
SHIBATA, T ;
TERANO, H ;
KOHSAKA, M ;
AOKI, H ;
IMANAKA, H .
JOURNAL OF ANTIBIOTICS, 1985, 38 (07) :926-935
[4]  
HUMPHRIES MJ, 1988, CANCER RES, V48, P1410
[5]   ON THE LEWIS ACID-CATALYZED CYCLOCONDENSATION OF IMINES WITH A SILOXYDIENE [J].
KERWIN, JF ;
DANISHEFSKY, S .
TETRAHEDRON LETTERS, 1982, 23 (37) :3739-3742
[6]   DIVERGENT SYNTHESES OF STEREOISOMERS OF SWAINSONINE - (-)-8-EPI-, (-)-8A-EPI- AND (-)-8,8A-DIEPI-SWAINSONINE [J].
KIM, YG ;
CHA, JK .
TETRAHEDRON LETTERS, 1989, 30 (42) :5721-5724
[7]  
KUNZ H, 1989, ANGEW CHEM, V101, P1041
[8]   ENANTIOMERICALLY PURE POLYHYDROXYLATED ACYLIMINIUM IONS - SYNTHESIS OF THE GLYCOSIDASE INHIBITORS (-)-SWAINSONINE AND (+)-CASTANOSPERMINE [J].
MILLER, SA ;
CHAMBERLIN, AR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8100-8112
[9]   (1S,2R,8R,8AR)-1,2,8-TRIHYDROXYOCTAHYDROINDOLIZINE (SWAINSONINE), AN ALPHA-MANNOSIDASE INHIBITOR FROM RHIZOCTONIA-LEGUMINICOLA [J].
SCHNEIDER, MJ ;
UNGEMACH, FS ;
BROQUIST, HP ;
HARRIS, TM .
TETRAHEDRON, 1983, 39 (01) :29-32
[10]   SYNTHESES OF (-)-8-EPI-SWAINSONINE AND (-)-1,8-DI-EPI-SWAINSONINE, STEREOISOMERS OF PHYSIOLOGICALLY INTERESTING INDOLIZIDINE ALKALOID, SWAINSONINE [J].
TADANO, K ;
IIMURA, Y ;
HOTTA, Y ;
FUKABORI, C ;
SUAMI, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (12) :3885-3892