Abstract
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.
Original language | English |
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Pages (from-to) | 563-597 |
Number of pages | 35 |
Journal | Heterocycles |
Volume | 82 |
Issue number | 1 |
DOIs | |
Publication status | Published - 2010 Dec 1 |
ASJC Scopus subject areas
- Analytical Chemistry
- Pharmacology
- Organic Chemistry