TOTAL SYNTHESIS OF THE INDOLE ALKALOID (+/-)-TACAMINE

被引：11
作者：
LOUNASMAA, M
BELLE, DD
TOLVANEN, A
机构：
[1] Laboratory for Organic and Bioorganic Chemistry, Technical University of Helsinki
来源：
TETRAHEDRON LETTERS | 1994年 / 35卷 / 33期
关键词：
D O I：
10.1016/0040-4039(94)88102-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The mixture of pentacyclic intermediates (4) was successfully converted into the pharmacologically interesting indole alkaloid (+/-)-tacamine (1). In a similar manner, the two unnatural isomers of 1, (+/-)-14-epitacamine (9) and (+/-)-14-epi-16-epitacamine (10), were obtained from intermediate 7. The key reaction, an acid-catalyzed displacement of the dimethylamino group with the hydroxyl group, is believed to take place via an iminium intermediate.
引用
收藏
页码：6151 / 6154
页数：4
相关论文
共 9 条
[1]  
IHARA M, 1994, HETEROCYCLES, V37, P289
[2]   PARTIAL SYNTHESIS OF (20S)-PSI-VINCAMINE AND (20S)-EPI-16 PSI-VINCAMINE [J].
LEMEN, J ;
CARONSIGAUT, C ;
HUGEL, G ;
LEMENOLIVER, L ;
LEVY, J .
HELVETICA CHIMICA ACTA, 1978, 61 (02) :566-570
[3]  
Lounasmaa M., 1992, ALKALOIDS, V42, P1
[4]  
MASSIOT G, 1982, B SOC CHIM FR II-CH, P185
[5]  
SZABO L, 1986, HETEROCYCLES, V24, P1517
[6]  
TAESOTIKUL T, 1990, Planta Medica, V56, P688, DOI 10.1055/s-2006-961365
[7]   ALDEHYDE INTERMEDIATES IN THE SYNTHESIS OF TACAMINE-TYPE INDOLE ALKALOIDS - PREPARATION OF (+/-)-APOTACAMINE [J].
TOLVANEN, A ;
BELLE, DD ;
LOUNASMAA, M .
HELVETICA CHIMICA ACTA, 1994, 77 (03) :709-715
[8]  
VANBEEK, 1984, TETRAHEDRON, V43, P737
[9]   TACAMINE, THE 1ST EXAMPLE OF A NEW CLASS OF INDOLE ALKALOIDS [J].
VANBEEK, TA ;
LANKHORST, PP ;
VERPOORTE, R ;
SVENDSEN, AB .
TETRAHEDRON LETTERS, 1982, 23 (46) :4827-4830
1