STUDIES ON THE ENANTIOSPECIFIC SYNTHESIS OF OXINDOLE ALKALOIDS

被引:25
作者
PETERSON, AC [1 ]
COOK, JM [1 ]
机构
[1] UNIV WISCONSIN,DEPT CHEM,MILWAUKEE,WI 53201
关键词
D O I
10.1016/S0040-4039(00)76997-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The optically active N-a-methyl, N-b-benzyltetracyclic ketone 1 was converted into either diastereomeric spirocyclic oxindole 2a (91:9) or 2b (97:3) with high diastereoselectivity on prudent choice of osmium reagents. Oxindole 2a is now available in enantiospecific form for the synthesis of Alstonia alkaloids while diastereomer 2b can be employed for the preparation of Gardneria and Voacanga bases.
引用
收藏
页码:2651 / 2654
页数:4
相关论文
共 20 条
[1]   CATALYTIC ASYMMETRIC-SYNTHESIS OF QUARTERNARY CARBON CENTERS - PALLADIUM-CATALYZED FORMATION OF EITHER ENANTIOMER OF SPIROOXINDOLES AND RELATED SPIROCYCLICS USING A SINGLE ENANTIOMER OF A CHIRAL DIPHOSPHINE LIGAND [J].
ASHIMORI, A ;
OVERMAN, LE .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17) :4571-4572
[2]   GENERAL-APPROACH FOR THE SYNTHESIS OF MACROLINE/SARPAGINE ALKALOIDS - THE TOTAL SYNTHESIS OF (+)-MACROLINE [J].
BI, YZ ;
COOK, JM .
TETRAHEDRON LETTERS, 1993, 34 (28) :4501-4504
[3]  
BRAEKMAN JC, 1969, B SOC CHIM BELG, V78, P523
[4]   ALSTONIA ALKALOIDS .11. ALKALOIDS OF ALSTONIA-MUELLERIANA [J].
ELDERFIE.RC ;
GILMAN, RE .
PHYTOCHEMISTRY, 1972, 11 (01) :339-&
[5]   ENANTIOSPECIFIC TOTAL SYNTHESIS OF THE AJMALINE RELATED ALKALOIDS (-)-SUAVEOLINE, (-)-RAUMACLINE, AND (-)-N(B)-METHYLRAUMACLINE [J].
FU, XY ;
COOK, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (17) :6910-6912
[6]   BIOMIMETIC TRANSFORMATIONS AMONG MONOMERIC MACROLINE-RELATED INDOLE ALKALOIDS [J].
GARNICK, RL ;
LEQUESNE, PW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (13) :4213-4219
[7]   SYNTHESIS OF ARISTOTELIA-TYPE ALKALOIDS .12. TOTAL SYNTHESIS OF (-)-TASMANINE - STEREOELECTRONIC FACTORS THAT CONTROL THE REARRANGEMENT OF 3H-INDOL-3-OL DERIVATIVES TO OXINDOLES (= 1,3-DIHYDRO-2H-INDOL-2-ONES) OR TO PSEUDOINDOXYLS (= 1,2-DIHYDRO-3H-INDOL-3-ONES) [J].
GULLER, R ;
BORSCHBERG, HJ .
HELVETICA CHIMICA ACTA, 1993, 76 (05) :1847-1862
[8]  
HAMAKER LK, 1994, IN PRESS ALKALOIDS C
[9]  
HOLLINSHEAD SP, 1989, HETEROCYCLES, V29, P529
[10]  
NORDMAN CE, 1963, J AM CHEM SOC, V85, P363