Highly diastereoselective inverse electron demand (IED) Diels-Alder reaction mediated by chiral salen-AICI complex: the first, target-oriented synthesis of pyranoquinolines as potential antibacterial agents

The first, target-oriented synthesis of pyranoquinolines as potential antibacterial agents by inverse electron demand (IED) Diels-Alder reaction using chiral salen-AlCl complex has been accomplished, the reactions proceed with moderate yields, and a very high degree of diastereoselectivity (>90%). The diastereoselectivity-enhanced pyranoquinolines exhibit potential bactericidal activity against seven strains of pathogenic grain-negative bacteria. (C) 2004 Elsevier Ltd. All rights reserved.