The Palladium-Catalyzed Preparation of Condensed Tetracyclic Heterocycles and their Application to the Synthesis of rac-Mangochinine

Abstract

Dihydroisoquinoline derivatives and their analogues, prepared by the Bischler-Napieralsky reaction, were converted to their indole-fused derivatives. Scope and limitations of the palladium-catalyzed reaction, proceeding through the tautomeric enamine forms of these compounds, were studied and the process was extended to the preparation of racemic mangochinine.

Key words

ring closure - palladium - catalysis - indoles - natural products

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1

Present address: Department of Chemistry, Faculty of Veterinary Sciences, Szent István University, 1078 Budapest, István u. 2, Hungary.

2

Present address: Chinoin Rt., 1045 Budapest, Tó u. 1-5., Hungary.