Study on the NBS-Induced Rearrangement of 2-tert-Prenyltryptamines

被引：12

作者：

Adla, Santosh Kumar ^{[1
]}

Golz, Gregor ^{[1
]}

Jones, Peter G. ^{[1
]}

Lindel, Thomas ^{[1
]}

机构：

[1] Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ Inorgan & Analyt Chem, D-38106 Braunschweig, Germany

来源：

SYNTHESIS-STUTTGART | 2010年 / 13期

关键词：

alkaloids; flustramines; indole; marine natural products; prenyl migration; N-BROMOSUCCINIMIDE; BRYOZOAN; BREVIANAMIDE; DERIVATIVES; BROMINATION; ALLYLATION; ALCOHOLS; INDOLES; SINGLE; AMINES;

D O I：

10.1055/s-0029-1218811

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 2-tert-prenyltryptamines with N-bromosuccinimide gives clean access to the marine natural product flustramine C and analogues with the tert-prenyl group shifted to the 3a-position of the resulting pyrrolo[2,3-b]indole (70-80%). Dihydroflustramine C was obtained by DIBAL-H reduction of flustramine C. Bromination or N-methylation of the indole moiety does not influence the course of the rearrangement.

引用

收藏

页码：2161 / 2170

页数：10

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