Total synthesis of (+)-cylindradine A.
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.
Department 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.
Makoto
M
Iwata
Kyohei
K
Kanoh
Takuya
T
Imaoka
Kazuo
K
Nagasawa
D001966:Bromine / Q000737:chemistry; D003500:Cyclization; D019791:Guanidine / Q000737:chemistry; D007202:Indicators and Reagents; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D011758:Pyrroles; C552501:cylindradine A; D019791:Guanidine; D001966:Bromine