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First asymmetric synthesis of (-)-lintetralin via intramolecular Friedel-Crafts-type cyclization
Dieter Enders1, Giuseppe Del Signore, Otto Mathias Berner
1Institute of Organic Chemistry, RWTH Aachen, Aachen, Germany. enders@rwth-aachen.de
Chirality
|May 30, 2003
Abstract:
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.