Enantioselective syntheses of the indole alkaloid (+)-R-decarbomethoxytetrahydrosecodine and its enantiomer

被引：32

作者：

Amat, M ^{[1
]}

Pshenichnyi, G ^{[1
]}

Bosch, J ^{[1
]}

Molins, E ^{[1
]}

Miravitlles, C ^{[1
]}

机构：

[1] CSIC,INST CIENCIA MAT,CERDANYOLA 08193,SPAIN

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 11期

关键词：

D O I：

10.1016/0957-4166(96)00405-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The alkaloid (+)-R-decarbomethoxytetrahydrosecodine (+)-1 has been synthesized by alkylation of (R)-3-ethylpiperidine with 3-(2-bromoethyl)-2-ethylindole (7). The required enantiopure piperidine was prepared by alkylation of the chiral non-racemic oxazolopiperidone (+)-trans-8 followed by reduction of the lactam carbonyl group and removal of the chiral auxiliary, whereas tryptophyl bromide 7 was obtained by reaction of N-silyl-3-lithioindole 5 with ethylene oxide followed by treatment with PBr3. The enantiomer of the natural product was prepared in a similar way, starting from (-)-trans-8. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：3091 / 3094

页数：4

共 19 条

[1] Synthesis of enantiopure piperidines. Total synthesis of (2R,6S)-2-methyl-6-propylpiperidine [(-)-dihydropinidine] [J].