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Molecules 2007, 12(2), 194-204; doi:10.3390/12020194

Synthesis of 2,5-Disubstituted Octahydroquinolin-4-ones via anIntramolecular Hetero Diels-Alder Reaction

,  and *
Instituto Universitario de Bio-Orgánica “Antonio González”, Departamento de Química Orgánica, Universidad de La Laguna, 38206 La Laguna, Tenerife, Spain
* Author to whom correspondence should be addressed.
Received: 25 January 2007 / Revised: 13 February 2007 / Accepted: 13 February 2007 / Published: 19 February 2007
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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.
Keywords: Hetero Diels-Alder;alkaloids;octahydroquinolone Hetero Diels-Alder; alkaloids; octahydroquinolone
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Ruiz, J.M.; Afonso, M.M.; Palenzuela, J.A. Synthesis of 2,5-Disubstituted Octahydroquinolin-4-ones via anIntramolecular Hetero Diels-Alder Reaction. Molecules 2007, 12, 194-204.

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