Concise Synthesis of the CDE Ring System of Tetrahydroisoquinoline Alkaloids Using Carbophilic Lewis Acid-Catalyzed Hydroamidation and Oxidative Friedel−Crafts Cyclization
Shingo Obika
Yoshizumi Yasui
Reiko Yanada
Yoshiji Takemoto
10.1021/jo800898k.s001
https://acs.figshare.com/articles/journal_contribution/Concise_Synthesis_of_the_CDE_Ring_System_of_Tetrahydroisoquinoline_Alkaloids_Using_Carbophilic_Lewis_Acid_Catalyzed_Hydroamidation_and_Oxidative_Friedel_Crafts_Cyclization/2929876
A concise synthesis of the CDE ring system of the tetrahydroisoquinoline antitumor alkaloids such as saframycins, renieramycins, and ecteinascidins has been developed. Both Au(I)-catalyzed intramolecular hydroamidation of alkynylamide and NBS-mediated oxidative Friedel−Crafts cyclization of the resulting 2-ketopiperazine were utilized as key reactions.
2008-07-04 00:00:00
Concise Synthesis
Cyclization
oxidative
intramolecular
hydroamidation
ketopiperazine
cyclization
Oxidative
CDE Ring System
synthesis
Friedel
saframycin
ecteinascidin
CDE ring system
Lewis
renieramycin
alkynylamide
Carbophilic
Hydroamidation
Tetrahydroisoquinoline Alkaloids
tetrahydroisoquinoline antitumor alkaloids