A Novel Stereoselective Synthesis of <Emphasis Type="Italic">cis</Emphasis>-Configured Erythrinane and Erythrinane Type Analogues |
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Authors: | Email author" target="_blank">Eberhard?ReimannEmail author Christian?Ettmayr |
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Institution: | (1) Department Pharmazie – Zentrum für Pharmaforschung, Ludwigs-Maximilians-Universität München, D-81377, München, Germany |
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Abstract: | Summary. N-Alkylation of certain angularly substituted heterocycles by C2- and C3-units provided appropriate precursors to construct stereoselectively the erythrinanone and several erythrinanone type analogues by intramolecular Friedel-Crafts acylation. The resulting aromatic ketones were catalytically reduced affording the corresponding parent frameworks including the hitherto unknown tetracyclus A-norschelhammerane. On the other hand, the stereoselective reduction of the carbonyl moiety offered a convenient approach to 11-hydroxylated erythrinanes with the natural occurring -configuration. The structures and the stereochemistry of the target compounds were proved by NMR spectroscopy.Part of PhD thesis, LMU München, D |
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Keywords: | -Hydroxy-15-methoxyerythrinane," target="_blank">, Alkaloids, Spiro compounds, Diastereoselective cyclizations, Erythrinane type frameworks, 11-Hydroxy-15-methoxyerythrinane, |
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