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A concise synthesis of siphonodictidine
Charles W Jefford1, Jean-Claude Rossier, John Boukouvalas
1Department of Organic Chemistry, University of Geneva, 30 quai Ernest-Ansermet, 1211 Geneva 4, Switzerland. Charles.Jefford@chiorg.unige.ch
Journal of Natural Products
|August 31, 2004
Abstract:
Siphonodictidine (1) has been synthesized for the first time in a concise and regiocontrolled manner by using 2-(tert-butyldimethylsiloxy)-3-methylfuran (6) as the crucial building block. The silver trifluoroacetate-induced alkylation of 6 with omega-bromogeranyl acetate 7 gave the key gamma-lactone intermediate 8, which on subsequent reduction, conversion of the hydroxyl into the amino group, and amidination afforded siphonodictidine (1) in an overall yield of 25.7% from 6.