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

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

Juan M. Ruiz, Maria M. Afonso and J. Antonio Palenzuela* email
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; in revised form: 13 February 2007 / Accepted: 13 February 2007 / Published: 19 February 2007
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Abstract: 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

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MDPI and ACS Style

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.

AMA Style

Ruiz JM, Afonso MM, Palenzuela JA. Synthesis of 2,5-Disubstituted Octahydroquinolin-4-ones via anIntramolecular Hetero Diels-Alder Reaction. Molecules. 2007; 12(2):194-204.

Chicago/Turabian Style

Ruiz, Juan M.; Afonso, Maria M.; Palenzuela, J. A. 2007. "Synthesis of 2,5-Disubstituted Octahydroquinolin-4-ones via anIntramolecular Hetero Diels-Alder Reaction." Molecules 12, no. 2: 194-204.

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