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Paper | Special issue | Vol 88, No. 1, 2014, pp.297-308
Published online, 11th June, 2013
DOI: 10.3987/COM-13-S(S)16
Total Synthesis of the Benzo[c]phenanthridine Alkaloids, Terihanine and Isoterihanine, and Their Antitumor Activity

Yuhki Kurata, Tominari Choshi,* Yuhsuke Ishihara, Noriyuki Hatae, Takashi Nishiyama, and Satoshi Hibino*

*Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan

Abstract

A new total synthesis of terihanine (2a) and isoterihanine (2b) was established by our new bond formation between the C4b and N5 positions of the benzo[c]phenanthridine ring based on a microwave-assisted thermal electrocyclic reaction of 2-cycloalkenylbenzaldoxime as an aza 6π-electron system. In addition, the antitumor activity of these synthesized compounds, including nitidine and nornitidine was evaluated in HCT-116 cells.