Synthesis of 2,5-disubstituted octahydroquinolin-4-ones via anintramolecular hetero Diels-Alder reaction

A route for the preparation of 2,5-disubstituted octahydroquinolin-4-ones, synthetic precursors of the decahydroquinoline-type toxins, is presented. The key steps are an asymmetric epoxidation and an intramolecular hetero Diels-Alder reaction between an activated diene and an imine. The presence of...

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Veröffentlicht in:	Molecules (Basel, Switzerland) Switzerland), 2007-02, Vol.12 (2), p.194-204
Hauptverfasser:	Ruiz, Juan M, Afonso, Maria M, Palenzuela, J Antonio
Format:	Artikel
Sprache:	eng
Schlagworte:	Alcohol alkaloids Catalysis Cyclization Hetero Diels-Alder Heterocyclic Compounds, 2-Ring - chemical synthesis Heterocyclic Compounds, 2-Ring - chemistry Magnetic Resonance Spectroscopy Molecular Conformation Molecular Structure octahydroquinolone Oxidation Quinolines - chemical synthesis Quinolines - chemistry Reagents Stereoisomerism
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Zusammenfassung:	A route for the preparation of 2,5-disubstituted octahydroquinolin-4-ones, synthetic precursors of the decahydroquinoline-type toxins, is presented. The key steps are an asymmetric epoxidation and an intramolecular hetero Diels-Alder reaction between an activated diene and an imine. The presence of an allylic stereogenic center induces some selectivity and thus only two cycloadducts are obtained in 70:30 ratio and good yield.
ISSN:	1420-3049 1420-3049
DOI:	10.3390/12020194