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.
Enders
Dieter
D
Institute of Organic Chemistry, RWTH Aachen, Aachen, Germany. enders@rwth-aachen.de
Del Signore
Giuseppe
G
Berner
Otto Mathias
OM
D007202:Indicators and Reagents; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D007202:Indicators and Reagents; D017705:Lignans; C476404:lintetralin