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Synfacts 2006(4): 0311-0311
DOI: 10.1055/s-2006-932025
DOI: 10.1055/s-2006-932025
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York
Synthesis of (-)-Eudistomin C
T. Yamashita, N. Kawai, H. Tokuyama, T. Fukuyama*
University of Tokyo, Japan
Further Information
Publication History
Publication Date:
24 March 2006 (online)
Significance
The tetrahydro-β-carboline core of (-)-Eudistomin C was constructed via a Brønsted acid catalyzed diastereoselective Pictet-Spengler reaction. The unusual oxathiazepine core, containing three heteroatoms and two stereocenters, was synthesized using an intramolecular thiol alkylation. (-)-Eudistomin C is a marine alkaloid, which displays antiviral, antitumour and antimicrobial activity.