Concise synthesis of the CDE ring system of tetrahydroisoquinoline alkaloids using carbophilic Lewis acid-catalyzed hydroamidation and oxidative Friedel-Crafts cyclization.
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.
Obika
Shingo
S
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
Yasui
Yoshizumi
Y
Yanada
Reiko
R
Takemoto
Yoshiji
Y
D000470:Alkaloids / Q000138:chemical synthesis*; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis*
D000470:Alkaloids; D000970:Antineoplastic Agents; D044005:Tetrahydroisoquinolines