ACYLNITRILIUM ION INITIATED HETEROANNULATIONS IN ALKALOID SYNTHESIS - AN EFFICIENT, STEREOCONTROLLED, TOTAL SYNTHESIS OF THE ORCHIDACEAE ALKALOID (+/-)-DENDROBINE

被引：47

作者：

LEE, CH ^{[1
]}

WESTLING, M ^{[1
]}

LIVINGHOUSE, T ^{[1
]}

WILLIAMS, AC ^{[1
]}

机构：

[1] MONTANA STATE UNIV,DEPT CHEM,BOZEMAN,MT 59717

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1992年 / 114卷 / 11期

关键词：

D O I：

10.1021/ja00037a009

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise total synthesis of (+/-)-dendrobine is described that proceeds in eight steps from 2-methylcyclopent-2-en-1-one. The key transformation in this approach is the silver ion mediated cyclocondensation of the isonitrile 6 with the acyl chloride 5. This highly convergent reaction proceeds in excellent (88%) overall yield to provide the DELTA-1-pyrroline 4.

引用

页码：4089 / 4095

页数：7

共 41 条

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