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Catalysis-based enantioselective total synthesis of the macrocyclic spermidine alkaloid isooncinotine

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Scheiper,  Bodo
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Glorius,  Frank
Research Group Glorius, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Leitner,  Andreas
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Scheiper, B., Glorius, F., Leitner, A., & Fürstner, A. (2004). Catalysis-based enantioselective total synthesis of the macrocyclic spermidine alkaloid isooncinotine. Proceedings of the National Academy of Sciences of the United States of America, 101(33), 11960-11965. doi:10.1073/pnas.0401322101.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-96CD-7
Abstract
A concise and efficient total synthesis of the spermidine alkaloid (-)-isooncinotine (1) incorporating a 22-membered lactam ring is outlined. The approach is largely catalysis-based, involving a selective iron-catalyzed alkyl–aryl cross-coupling reaction of a difunctionalized pyridine substrate, a heterogeneous asymmetric hydrogenation step to set the chiral center of the target, and a highly integrated ring-closing metathesis/hydrogenation sequence to forge the saturated macrocyclic edifice in a single operation.