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Synthesis of (+)- and (-)-Batzelladine C Based on a Cyclization/Carbonylation/Double Cyclization Cascade: Revision of
Tianci Yue1, Taichi Kusakabe1, Kyoka Someya1
1Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan.
Abstract:
Syntheses of guanidino alkaloids (+)- and (-)-batzelladine C are described. The key feature of the syntheses is the cyclization/carbonylation/double cyclization cascade of optically active propargyl guanidine. The tricyclic guanidino cores bearing three stereogenic centers and an ester functionality were constructed in a single step. The esters with a hydroxy group were then converted into (+)- and (-)-batzelladine C. The absolute configuration of natural (-)-batzelladine C was revised to the (11S,13R,15S) configuration.
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