A revised structure for the piperidine alkaloid andrachamine

被引：20

作者：

Mill, S ^{[1
]}

Hootele, C ^{[1
]}

机构：

[1] FREE UNIV BRUSSELS,FAC SCI,DEPT ORGAN CHEM,B-1050 BRUSSELS,BELGIUM

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1996年 / 74卷 / 12期

关键词：

N-acyliminium; piperidine; alkaloid; andrachamine;

D O I：

10.1139/v96-272

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new method for the synthesis of trans-2,6-disubstituted piperidine derivatives is described. The transformation of cyclic alpha-methoxycarbamates 5 and 6 affords trans ketones 17 and 18. The synthesis of diols 1-4 from 17 and 1S has shown thar the structure proposed in the literature for the piperidine alkaloid andrachamine is incorrect. A reexamination of the original spectral data of this alkaloid suggested that it is a mesa 2,6-disubstituted piperidine derivative. Unambiguous syntheses of 23 and 24 and comparison with a sample of andrachamine have established that this alkaloid possesses structure 23.

引用

页码：2434 / 2443

页数：10

共 20 条

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