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Short Paper | Regular issue | Vol 94, No. 3, 2017, pp.503-514
Published online, 17th March, 2017
DOI: 10.3987/COM-16-13638
■ Synthesis of 6,7-Dihydro-9,10-dimethoxydibenzo[a,f]quinolizinium Salt and Its D-Ring Substituted Derivatives

Kazuo Yamazaki, Mai Aritake, Shungo Takamoto, Midori Tabata, Sachiko Yanagihara, Keisuke Uji, Kazuaki Ohyama, Kei Ogiso, Takumi Sugahara, Ai Tatara, Tetsuji Hosono, Keitaro Suzuki, and Masashi Ohba*

*Yokohama University of Pharmacy, Matano-cho, Totsuka-ku, Yokohama 245-0066, Japan

Abstract

Synthesis of 6,7-dihydro-9,10-dimethoxydibenzo[a,f]quinolizinium salt (2a) and its derivatives (2b–g) substituted at the D ring has been achieved from 3-(2-bromoaryl)propanoic acid (3) in four steps for future examination of the inhibitory activity of these compounds against topoisomerase. The dihydrocarbostyrils (5a–g), key intermediates in this synthetic scheme, were prepared from the amides (4a–g) via intramolecular aryl amidation reactions.