Total synthesis of natural (+)-sesbanimide a and (-)-sesbanimide b |
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| Institution: | 1. School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, China;2. Institute of Chemistry, Jan Kochanowski University in Kielce, Kielce, Poland;3. Department of Organic Chemistry I, University of the Basque Country UPV/EHU, San Sebastián, Spain;4. Molecular Structure Analysis, German Cancer Research Center (DKFZ), Heidelberg, Germany;5. IKERBASQUE, Basque Foundation for Science, Bilbao, Spain |
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| Abstract: | The first total synthesis of natural (+)-sesbanimide A (1) and (-)-sesbanimide B (2), potent antitumor alkaloids isolated from the seeds of the leguminous plant, Sesbania drummondii, has been accomplished starting from D-(+)-xylose. This total synthesis involves efficient construction of the optically active AB-ring system from D-(+)-xylose, introduction of the C5-unit into the AB-ring system in a form of exo-methylene-γ-lactone, and elaboration of the labile C-ring system at the last stage of the synthesis. The absolute configurations of natural 1 and 2 could be obviously established by our total synthesis. |
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