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 an allylic stereogenic center induces some selectivity and thus only two cycloadducts are obtained in 70:30 ratio and good yield.
Ruiz
Juan M
JM
Instituto Universitario de Bio-Orgánica Antonio González, Departamento de Química Orgánica, Universidad de La Laguna, 38206 La Laguna, Tenerife, Spain.
Afonso
Maria M
MM
Palenzuela
J Antonio
JA
D002384:Catalysis; D003500:Cyclization; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D006574:Heterocyclic Compounds, 2-Ring; D011804:Quinolines