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Paper | Special issue | Vol 99, No. 1, 2019, pp.415-424
Published online, 16th October, 2018
DOI: 10.3987/COM-18-S(F)36
Concise Synthesis of Kalasinamide, Marcanine A, and Geovanine, and Antiproliferative Activity Evaluation of Their Azaanthracenones

Takashi Nishiyama, Noriyuki Hatae,* Kyohko Chikaraishi, Keisuke Uchida, Chika Yokoyama, Satoshi Hibino, and Tominari Choshi*

*Graduate School of Pharmacy & Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan


The total syntheses of kalasinamide (1), marcanine A (2), and geovanine (3) have been conducted by the formation of a fused pyridone-ring azaanthracenone core based on a Curtius rearrangement that is followed by the microwave-assisted thermal electrocyclization of an isocyanato-containing 2-azahexatriene system. The antiproliferative activities of these synthetic compounds against the HCT-116 colon tumor cells were evaluated by the MTT assay.