STEREOSELECTIVE PREPARATION OF INDOLOQUINOLIZIDINE N-OXIDES - PREDOMINANT CONFORMATIONS

被引:17
作者
LOUNASMAA, M
TAMMINEN, T
机构
[1] Laboratory for Organic and Bioorganic Chemistry, Technical University of Helsinki
关键词
D O I
10.1016/S0040-4020(01)87093-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereoselective preparation of indoloquinolizidine N-oxides possessing the N(b)-oxygen - C(12b) -hydrogen relationship, trans or cis at will, is described. Contribution of the different conformations to the conformational equilibrium is studied by C-13 NMR spectroscopy, and significance of the N(b)-oxygen - C(12b)-hydrogen relationship for the regioselective transformation of indoloquinolizidine N-oxides to the corresponding iminium ions is discussed.
引用
收藏
页码:2879 / 2894
页数:16
相关论文
共 22 条
[1]  
CHEVOLOT L, 1976, B SOC CHIM FR II-CH, P1222
[2]   AN IMPROVED PREPARATION OF TERTIARY AMINE N-OXIDES [J].
CRAIG, JC ;
PURUSHOT.KK .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (05) :1721-&
[3]  
DAMAK M, 1976, TETRAHEDRON LETT, P4731
[4]  
HUSSON HP, 1980, INDOLE BIOGENETICALL, P185
[5]   STEREOSELECTIVE SYNTHESIS OF DL-18,19-DIHYDROANTIRHINE AND DL-3-EPI-18,19-DIHYDROANTIRHINE [J].
LOUNASMAA, M ;
JOKELA, R .
TETRAHEDRON, 1989, 45 (23) :7449-7458
[6]   STEREOREGULATION OF THE C(12B)H-C(2)H RELATIONSHIP IN THE PREPARATION OF 2-SUBSTITUTED 1,2,3,4,6,7,12,12B-OCTAHYDROINDOLO[2,3-A]QUINOLIZINES [J].
LOUNASMAA, M ;
JOKELA, R .
TETRAHEDRON, 1989, 45 (12) :3975-3992
[7]   SYNTHETIC STUDIES IN ALKALOID FIELD .10. PREPARATION AND STEREOSTRUCTURE DETERMINATION OF SEVERAL INDOLO[2,3-A]QUINOLIZINE DERIVATIVES [J].
LOUNASMAA, M ;
MERIKALLIO, H ;
PUHAKKA, M .
TETRAHEDRON, 1978, 34 (19) :2995-2999
[8]   A 400 MHZ H-1-NMR STUDY OF THE 8 BASIC HETEROYOHIMBINE ALKALOIDS [J].
LOUNASMAA, M ;
KAN, SK .
TETRAHEDRON, 1980, 36 (11) :1607-1611
[10]   STEREOREGULATION IN THE PREPARATION OF 1-MONOSUBSTITUTED AND 3-MONOSUBSTITUTED 1,2,3,4,6,7,12,12B-OCTAHYDROINDOLO[2,3-A]QUINOLIZINES [J].
LOUNASMAA, M ;
JOKELA, R ;
TIRKKONEN, B ;
TAMMINEN, T .
TETRAHEDRON, 1989, 45 (23) :7615-7630