Highly diastereoselective synthesis of new heterolignan-like 6,7-methylendioxy-tetrahydroquinolines using the clove bud essential oil as raw material

✍ Scribed by Diego R. Merchan Arenas; Fernando A. Rojas Ruíz; Vladimir V. Kouznetsov

• Book ID: 104098865
• Publisher: Elsevier Science
• Year: 2011
• Tongue: French
• Weight: 428 KB
• Volume: 52
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2011.01.083

✦ Synopsis

The diastereoselective synthesis toward novel heterolignan-like 2-aryl-4-(4-hydroxy-3-methoxyphenyl)-6,7-methylendioxy-1,2,3,4-tetrahydroquinolines using for the first time clove bud essential oil as a renewable material was carried out. The synthetic protocol consisted of the hydrodistillation of dried flower buds, the solid base-catalyzed isomerization of the obtained essential oil enriched with eugenol in order to give isoeugenol and its participation, as a chemical reagent (dienophile) in the BF 3 ÁOEt 2 -catalyzed three component Povarov reaction, without previous purification. Final products were obtained as racemic mixtures of new trans-2,4-diaryl-r-3-Me-1,2,3,4-tetrahydroquinolines in moderate to good yields.