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

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.

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 Creators:
Scheiper, Bodo1, Author              
Glorius, Frank2, Author              
Leitner, Andreas1, Author              
Fürstner, Alois1, Author              
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Research Group Glorius, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445602              

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 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.

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Language(s): eng - English
 Dates: 2004-02-252004-04-062004-08-17
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: eDoc: 218328
DOI: 10.1073/pnas.0401322101
ISI: 000223410100010
 Degree: -

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Title: Proceedings of the National Academy of Sciences of the United States of America
  Other : Proc. Natl. Acad. Sci. USA
Source Genre: Journal
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Publ. Info: Washington, DC : National Academy of Sciences
Pages: - Volume / Issue: 101 (33) Sequence Number: - Start / End Page: 11960 - 11965 Identifier: ISSN: 0027-8424
CoNE: https://pure.mpg.de/cone/journals/resource/954925427230