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Paper | Special issue | Vol 82, No. 1, 2010, pp.563-579
Published online, 11th June, 2010
DOI: 10.3987/COM-10-S(E)27
Total Synthesis of (+)- and (-)-Galanthamine

Tomoaki Kato, Hiroki Tanimoto, Hisako Yamada, and Noritaka Chida*

*Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku Yokohama 223-8522, Japan


The stereoselective total synthesis of (+)-galanthamine [(+)-1], an antipode of the natural product, and (–)-galanthamine [(–)-1] starting from D-glucose is described. The cyclohexene unit in (+)-1 was prepared in an optically active form from D-glucose using Ferrier’s carbocyclization reaction, and the benzylic quaternary carbon was stereoselectively generated via chirality transfer by Johnson- or Eschenmoser-Claisen rearrangement. The dibenzofuran skeleton was effectively constructed by the bromonium ion-mediated intramolecular dealkylating etherification. After the introduction of a carbon-carbon double bond, the Pictet-Spengler type cyclization, followed by reduction of an amide function afforded (+)-1. Starting from D-glucose, (–)-galanthamine [(–)-1] was also totally synthesized.