THE SYNTHESIS OF ROEHARMINE AND (-)-1,2,3,4-TETRAHYDROROEHARMINE

被引：30

作者：

REDDY, MS ^{[1
]}

COOK, JM ^{[1
]}

机构：

[1] UNIV WISCONSIN,DEPT CHEM,MILWAUKEE,WI 53201

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(00)73513-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of roeharmine 1 as well as an enantiospecific synthesis of (-)-1,2,3,4-tetrahydroroeharmine 2 has been achieved via the Pictet-Spengler reaction as a key step. The optical rotation of synthetic (-)-2 was found to be higher than that reported for the natural product. A possible mechanism for the racemization of 2 upon exposure to acid has been proposed and serves as a warning to alkaloid chemists who isolate ring-A alkoxylated indole alkaloids under acidic conditions.

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页码：5413 / 5416

页数：4

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