TOTAL SYNTHESIS OF STRYCHNAN AND ASPIDOSPERMATAN ALKALOIDS .3. THE TOTAL SYNTHESIS OF (+/-)-STRYCHNINE

被引：80

作者：

KUEHNE, ME

XU, F

机构：

[1] Department of Chemistry, University of Vermont, Burlington

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 26期

关键词：

D O I：

10.1021/jo00078a030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of N(b)-benzyl-2-[(methoxycarbonyl)methyl]tryptamine (3) with 4,4-dimethoxybut-2-en-1-al (6) provided, by a new condensation-electrocyclization reaction, the tetracyclic core 2 of strychnine (1). A 13-step elaboration of this compound gave a stereoselective synthesis of the racemic alkaloid.

引用

页码：7490 / 7497

页数：8

共 21 条

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[2]

COPE A, 1960, ORG REACTIONS, V11, P391

[3]

COPE A, 1960, ORG REACTIONS, V11, P390

[4]

Cope A. C., ORGANIC REACTIONS, P317