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Paper | Special issue | Vol 93, No. 1, 2016, pp.84-100
Published online, 24th August, 2015
DOI: 10.3987/COM-15-S(T)5
Total Synthesis of Carbazole-1,4-quinone Alkaloid Koeniginequinones A and B Based on a One-Pot Cyclocarbonylation Procedure from 2-Alkenyl-3-iodoiodoindole

Takashi Nishiyama, Nanase Satsuki, Satoshi Hibino,* Mami Fujii, Takumi Abe, Minoru Ishikura, and Tominari Choshi*

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


Total syntheses of koeniginequinones A and B, isolated from Murraya koenigii, were newly achieved by constructing of carbazole-1,4-quinone using a one-pot Pd-catalyzed cyclocarbonylation method with 2-(but-2-en-1-yl)-3-iodoindoles derived from known methyl 6-methoxyindole-2-carboxylate and methyl 5,6-dimethoxyindole-2-carboxylate, followed by desilylation, and an oxidation sequence.