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Paper | Regular issue | Vol 87, No. 2, 2013, pp.357-367
Published online, 17th December, 2012
DOI: 10.3987/COM-12-12630
First Total Syntheses of 1,3-Disubstituted β-Carboline Alkaloids, Dichotomide I and Marinacarbolines A-D

Shinji Tagawa, Tominari Choshi,* Asuka Okamoto, Takashi Nishiyama, Shiroh Watanabe, Noriyuki Hatae, and Satoshi Hibino*

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

Abstract

The first total syntheses of dichotomide I (1), and marinacarbolines A-D (3-6) were achieved in four steps from methyl 1-chloro-β-carboline-3-carboxlyate (9), which was previously used as a synthetic intermediate of dichotomine C. The required compound 9 was prepared in a six-step sequence including a microwave-assisted thermal electrocyclic reaction of a 1-azahexatriene system.