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Note | Regular issue | Vol 71, No. 7, 2007, pp.1623-1630
Published online, 24th April, 2007
DOI: 10.3987/COM-07-11062
Studies toward the Synthesis of Toddaquinoline by Intramolecular Cyclization

Georgeta Serban,* Yasumi Shigeta, Hiromi Nishioka, Hitoshi Abe, Yasuo Takeuchi, and Takashi Harayama*

*Faculty of Pharmaceutical Science, Okayama University, 1-1-1 Tsushima-naka, Okayama 700-8530, Japan

Abstract

-In connection with studies on the total synthesis of toddaquinoline (1), the synthesis of [1,3]dioxolo-[4’,5’:4,5]benzo[h]quinoline (1a), which is the tetracyclic core of 1, was investigated. Intramolecular benzene-pyridine coupling reactions of the monobromide (9) and dibromide (10), using a Pd reagent and Cu reagent, were evaluated to produce 1a in poor to moderate yields.