CYCLOADDITION REACTIONS OF CARBOHYDRATE-DERIVATIVES .4. SYNTHESIS OF A TETRAHYDROXYINDOLIZIDINE THROUGH A CYCLIC NITRONE PREPARED FROM D-XYLOSE

被引:54
作者
HERCZEGH, P [1 ]
KOVACS, I [1 ]
SZILAGYI, L [1 ]
VARGA, T [1 ]
DINYA, Z [1 ]
SZTARICSKAI, F [1 ]
机构
[1] LAJOS KOSSUTH UNIV,DEPT ORGAN CHEM,H-4010 DEBRECEN,HUNGARY
关键词
D O I
10.1016/S0040-4039(00)77531-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Intramolecular conjugate addition of the oxime from aldehyde 5 led to the formation of cyclic nitrone 6. 1,3-Dipolar cycloaddition of the latter with methyl acrylate gave the bicyclic 7 with high diastereoselection. Subsequent four-step transformation of 7 resulted in the tetrahydroxyindolizidine derivative 11.
引用
收藏
页码:1211 / 1214
页数:4
相关论文
共 13 条
[1]  
ALI SA, 1988, TETRAHEDRON, V44, P5911
[2]   REACTIVITY, REGIOCHEMISTRY, AND STEREOCHEMISTRY OF A CYCLIC NITRONE AND ITS ALPHA-KETO DERIVATIVE IN 1, 3-DIPOLAR CYCLO-ADDITION REACTIONS [J].
ALI, SA ;
WAZEER, MIM .
TETRAHEDRON, 1988, 44 (01) :187-193
[3]   TANDEM INTRAMOLECULAR MICHAEL ADDITION AND 1,3-DIPOLAR CYCLOADDITION REACTIONS OF OXIMES - VERSATILE NEW CARBON CARBON BOND FORMING METHODOLOGY [J].
ARMSTRONG, P ;
GRIGG, R ;
SURENDRAKUMAR, S ;
WARNOCK, WJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (17) :1327-1328
[4]   RECENT SYNTHETIC APPLICATIONS OF NITRONES - A REVIEW [J].
BALASUBRAMANIAN, N .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1985, 17 (01) :23-47
[5]   STEREOCHEMICAL STUDIES ON ESPERAMICINS - DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF HYDROXYAMINO SUGAR FRAGMENT [J].
GOLIK, J ;
WONG, H ;
KRISHNAN, B ;
VYAS, DM ;
DOYLE, TW .
TETRAHEDRON LETTERS, 1991, 32 (16) :1851-1854
[6]   X=Y - ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .35. GENERATION OF NITRONES FROM OXIMES - CLASS-3 PROCESSES - TANDEM INTRAMOLECULAR MICHAEL ADDITION (1,3-AZAPROTIO CYCLOTRANSFER) - INTERMOLECULAR 1,3-DIPOLAR CYCLOADDITION REACTIONS [J].
GRIGG, R ;
MARKANDU, J ;
PERRIOR, T ;
SURENDRAKUMAR, S ;
WARNOCK, WJ .
TETRAHEDRON, 1992, 48 (33) :6929-6952
[7]   CYCLOADDITION REACTIONS OF CARBOHYDRATE-DERIVATIVES .3. A NEW ROUTE TO SWAINSONINE ANALOGS [J].
HERCZEGH, P ;
KOVACS, I ;
SZILAGYI, L ;
ZSELY, M ;
SZTARICSKAI, F ;
BERECIBAR, A ;
OLESKER, A ;
LUKACS, G .
TETRAHEDRON LETTERS, 1992, 33 (22) :3133-3136
[8]   INTRAMOLECULAR REACTIONS OF COMPOUNDS DERIVED FROM SUGARS .2. STEREO-CONTROLLED INTRAMOLECULAR DIELS-ALDER CYCLIZATIONS OF 1,6(E,Z),8-NONATRIENES AND 1-AZA-6(E,Z),8-NONATRIENES [J].
HERCZEGH, P ;
ZSELY, M ;
SZILAGYI, L ;
BATTA, G ;
BAJZA, I ;
BOGNAR, R .
TETRAHEDRON, 1989, 45 (09) :2793-2802
[9]   CASTANOSPERMINE, A 1,6,7,8-TETRAHYDROXYOCTAHYDROINDOLIZINE ALKALOID, FROM SEEDS OF CASTANOSPERMUM-AUSTRALE [J].
HOHENSCHUTZ, LD ;
BELL, EA ;
JEWESS, PJ ;
LEWORTHY, DP ;
PRYCE, RJ ;
ARNOLD, E ;
CLARDY, J .
PHYTOCHEMISTRY, 1981, 20 (04) :811-814
[10]  
RAO CNR, 1963, CHEM APPLICATIONS IN, P453