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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 3.0).

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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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