Condensed Heteroaromatic Ring Systems. V. : Formal Synthesis of Matrine and Related Compounds Using Palladium-Catalyzed Carbon-Carbon Bond Formations as Key Reactions

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The iodination and subsequent dehydroxychlorination of 1, 6-naphthyridin-5(6H)-one gave 5-chloro-8-iodo-1, 6-naphthyridine, which was converted to the 5-methyoxy derivative. Starting from this compound, didehydromatrine was synthesized by using palladium-catalyzed cross-coupling reactions with ethyl acrylate and 3-butyn-1-ol, as key reactions. Similarly, nordehydro-α-matrinidine was synthesized through four steps from 8-bromo-1, 6-naphthyridine, obtained by the bromination o unsubstituted 1, 6-naphthyridine.