Stereoselective reactions: XIII. Total synthesis of (+)-sesbanine by a highly stereoselective cycloannelation reaction |
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| Affiliation: | 1. Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba, 260-8675, Japan;2. Molecular Chirality Research Center, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan;1. C4T (Colosseum Combinatorial Chemistry Centre for Technology) S.C.a r.l., Via della Ricerca Scientifica s.n.c., 00133 Rome, Italy;2. Department of Discovery, Dompé Farmaceutici SpA Research Center, via Campo di Pile, 67100 L’Aquila, Italy;3. Department of Discovery, Dompé Farmaceutici SpA, Research Center, via P. Castellino, 80131 Napoli, Italy;4. Department of Chemical Science and Technology, University of Rome ‘Tor Vergata’, 00133 Rome, Italy;1. LAQV-REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, P-4169-007 Porto, Portugal;2. Ciências Químicas e das Biomoléculas, Escola Superior de Saúde, Politécnico do Porto, P-4200-072 Porto, Portugal;3. i3S – Instituto de Investigação e Inovação em Saúde da Universidade do Porto, P-4200-393 Porto, Portugal;1. Department of Physical and Chemical Sciences, University of L’Aquila, via Vetoio, I-67100 L’Aquila, Italy;2. Department of Chemistry and Industrial Chemistry, University of Pisa, via G. Moruzzi 13, I-56124 Pisa, Italy;3. CIRCC, via Celso Ulpiani 27, I-70126 Bari, Italy |
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| Abstract: | An alkaloid sesbanine (1) was synthesized starting from 1-malic acid as a chiral four-carbon unit. The key step was a highly stereoselective cycloannelation reaction to form a chiral quaternary carbon center. By this synthesis, the absolute configuration of natural sesbanine was established to 1. Furthermore, sesbanine, in both optically active and racemic forms, was found to be marginaly cytotoxic, contrary to remarkable cytotoxicity reported. |
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