jo800898k_si_001.pdf (16.42 MB)
Concise Synthesis of the CDE Ring System of Tetrahydroisoquinoline Alkaloids Using Carbophilic Lewis Acid-Catalyzed Hydroamidation and Oxidative Friedel−Crafts Cyclization
journal contribution
posted on 2008-07-04, 00:00 authored by Shingo Obika, Yoshizumi Yasui, Reiko Yanada, Yoshiji TakemotoA 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.