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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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2007-02, Vol.12 (2), p.194-204
Main Authors: Ruiz, Juan M, Afonso, Maria M, Palenzuela, J Antonio
Format: Article
Language:English
Subjects:
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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Summary: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