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Concise synthesis of the CDE ring system of tetrahydroisoquinoline alkaloids using carbophilic Lewis acid-catalyzed hydroamidation and oxidative Friedel-Crafts cyclization

Authors :
Obika, Shingo
Yasui, Yoshizumi
Yanada, Reiko
Takemoto, Yoshiji
Source :
Journal of Organic Chemistry. July 4, 2008, Vol. 73 Issue 13, 5206-5209
Publication Year :
2008

Abstract

The development of a concise synthesis of the CDE ring system of the tetrahydroisoquinoline antitumor alkaloids such as saframycins, renieramycins, and ecteinascidins is reported. The key steps in the reaction include Au(I)-catalyzed intramolecular hydroamidation and NBS-mediated oxidative Friedel-Crafts cyclization.

Details

Language :
English
ISSN :
00223263
Volume :
73
Issue :
13
Database :
Gale General OneFile
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
edsgcl.182628217