Total synthesis of (+)- and (-)-galanthamine

Tomoaki Kato, Hiroki Tanimoto, Hisako Yamada, Noritaka Chida

Research output: Contribution to journalArticle

27 Citations (Scopus)

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 languageEnglish
Pages (from-to)563-597
Number of pages35
JournalHeterocycles
Volume82
Issue number1
DOIs
Publication statusPublished - 2010 Dec 1

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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