GENERAL METHODS OF SYNTHESIS OF INDOLE ALKALOIDS .7. SYNTHESES OF DL-DIHYDROGAMBIRTANNINE AND ASPIDOSPERMA-STRYCHNOS ALKALOID MODELS

被引：35

作者：

WENKERT, E

DAVE, KG

GNEWUCH, CT

SPRAGUE, PW

机构：

[1] Department of Chemistry, Indiana University, Bloomington

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1968年 / 90卷 / 19期

关键词：

D O I：

10.1021/ja01021a033

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of dimethyl isoquinoline-4,5-dicarboxylate and its four-step conversion into the indole alkaloid dihydrogambirtannine are reported. The preparation of methyl 3-(β-chloroethyl)-2-indoleacetate, its N-alkylation of several β-acylpyridines, and hydrogenation of the salts are described. The use of the resultant 2-piperideines and related 2-methylindole compounds in a study of the rarely observed β-indole cyclization process and the synthesis of Aspidosperma and Strychnos alkaloid models are portrayed. © 1968, American Chemical Society. All rights reserved.

引用

页码：5251 / &

共 21 条

[1]

CAVA MP, 1963, TETRAHEDRON LETT, P53

[2] THE REDUCTIVE CYCLIZATION OF INDOLYLETHYLISOQUINOLINIUM SALTS [J].