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Total synthesis of (+)-cylindradine A
Makoto Iwata1, Kyohei Kanoh, Takuya Imaoka
1Department of Biotechnology and Life Science, Faculty of Technology, Tokyo University of Agriculture and Technology, Naka-cho 2-24-16, Koganei, Tokyo 184-8588, Japan. Knaga@cc.tuat.ac.jp.
Chemical Communications (Cambridge, England)
|May 22, 2014
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.