The palladium-catalyzed preparation of condensed tetracyclic heterocycles and their application to the synthesis of rac-mangochinine

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 pr...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 8; pp. 1375 - 1385
Main Authors Vincze, Z, Biro, AB, Csekei, M, Timari, G, Kotschy, A
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 19.04.2006
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROUTE
DIBENZOPYRROCOLINE ALKALOIDS
HYDROGENATION
MORPHINE
ring closure
catalysis
natural products
indoles
LAUDANOSOLINE
palladium
AGENTS
DERIVATIVES
CYCLIZATION
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Summary: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.
ISSN:0039-7881
DOI:10.1055/s-2006-926410