First asymmetric synthesis of (-)-lintetralin via intramolecular Friedel-Crafts-type cyclization.

The asymmetric synthesis of an aryltetralin lignan, (-)-lintetralin, was achieved with an overall yield of 29% with seven steps. Key features of the synthesis are an asymmetric Strecker reaction, a diastereoselective Michael addition of the lithiated amino nitrile product to 5H-furan-2-one, and an intramolecular carbocationic cyclization to provide the desired ring skeleton with the correct configuration. Copyright 2003 Wiley-Liss, Inc.