FIRST-SYNTHESIS OF THE NOVEL GELSEMIUM ALKALOIDS, GELSELEGINE, GELSENICINE, AND GELSEDINE USING A BIOMIMETIC APPROACH

被引：44

作者：

TAKAYAMA, H ^{[1
]}

TOMINAGA, Y ^{[1
]}

KITAJIMA, M ^{[1
]}

AIMI, N ^{[1
]}

SAKAI, S ^{[1
]}

机构：

[1] CHIBA UNIV, FAC PHARMACEUT SCI, INAGE KU, CHIBA 263, JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 16期

关键词：

D O I：

10.1021/jo00095a010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Based on a suggested biogenetic sequence, a sarpagine-type indole alkaloid, gardnerine (7), was converted into three novel Gelsemium alkaloids, gelselegine (4), gelsenicine (6), and gelsedine (5). This first synthesis of these alkaloids involves stereoselective skeletal rearrangements, such as indole to oxindole transformations and conversion of humantenine-type compounds to gelselegine,as well as the synthesis of a characteristic N-a-methoxyoxindole function.

引用

页码：4381 / 4385

页数：5

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