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Issue 53, 2014
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Total synthesis of (+)-cylindradine A

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Abstract

Cylindradines A and B, members of the polycyclic pyrrole-imidazole alkaloids (PIAs), are the only congeners bearing a 3-carbamoylpyrrole unit among the PIAs. In this communication, we described a total synthesis of (+)-cylindradine A based on intramolecular Friedel–Crafts type cyclization of pyrrole-aldehyde and oxidative cyclization of tricyclic pyrrolopyrrolidine-guanidine with hypervalent iodine to construct the cyclic guanidine structure including the N,N′-aminal moiety.

Graphical abstract: Total synthesis of (+)-cylindradine A

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Publication details

The article was received on 07 Jan 2014, accepted on 04 May 2014 and first published on 08 May 2014


Article type: Communication
DOI: 10.1039/C4CC00137K
Author version available: Download Author version (PDF)
Citation: Chem. Commun., 2014,50, 6991-6994
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    Total synthesis of (+)-cylindradine A

    M. Iwata, K. Kanoh, T. Imaoka and K. Nagasawa, Chem. Commun., 2014, 50, 6991
    DOI: 10.1039/C4CC00137K

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