Stereocontrolled total synthesis of (-)-eudistomin C.
A stereocontrolled total synthesis of (-)-eudistomin C was accomplished in 18-step sequence with an overall yield of 7.7%. The synthesis features the diastereoselective Pictet-Spengler reaction of a tryptamine derivative and the Garner aldehyde catalyzed by Bronsted acids, and the unprecedented construction of the unusual oxathiazepine ring by intramolecular alkylation.
Yamashita
Tohru
T
Graduate School of Pharmaceutical Sciences, University of Tokyo, Bunkyo-ku, Tokyo 113-0033, Japan.
Kawai
Nobutaka
N
Tokuyama
Hidetoshi
H
Fukuyama
Tohru
T
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D000998:Antiviral Agents / Q000138:chemical synthesis*; D002243:Carbolines / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008956:Models, Chemical; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D002243:Carbolines; D007202:Indicators and Reagents; C507825:eudistomin C