title: Stereocontrolled total synthesis of (-)-eudistomin C.
abstract: 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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Tokyo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Tohru
authors.initials: T
authors.lastname: Yamashita
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Kawai
authors.forename: Hidetoshi
authors.initials: H
authors.lastname: Tokuyama
authors.forename: Tohru
authors.initials: T
authors.lastname: Fukuyama
mesh_terms: 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
chemical_list: D000970:Antineoplastic Agents; D000998:Antiviral Agents; D002243:Carbolines; D007202:Indicators and Reagents; C507825:eudistomin C