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Paper | Regular issue | Vol 91, No. 3, 2015, pp.537-549
Published online, 5th February, 2015
DOI: 10.3987/COM-14-13155
Novel Total Synthesis of the 2-Azaanthraquinone Alkaloid Scorpinone Using a Tandem Oxidation and Azaelectrocyclic Reaction

Tominari Choshi,* Miharu Hironaka, Miki Goto, Kaori Shimizu, Yuhki Kurata, Takashi Nishiyama, Noriyuki Hatae, and Satoshi Hibino*

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

Abstract

A new tandem oxidation and electrocyclic reaction of a 1-aza 6π-electron system derived from a known 3-hydroxynaphthalene derivative was developed for the synthesis of 2-azaanthraquinones. Total synthesis of scorpinone (1a) was achieved in seven steps using this new tandem reaction. In addition, the positional isomer, 7,9-dimethoxy-4-methylbenzo[g]isoquinoline-5,10-dione (1b) was also synthesized in the same way.