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

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Galantamine
Carbon
Glucose
Chirality
Cyclization
Biological Products
Skeleton
Amides
Ions

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cite this

Total synthesis of (+)- and (-)-galanthamine. / Kato, Tomoaki; Tanimoto, Hiroki; Yamada, Hisako; Chida, Noritaka.

In: Heterocycles, Vol. 82, No. 1, 2010, p. 563-597.

Research output: Contribution to journalArticle

Kato, T, Tanimoto, H, Yamada, H & Chida, N 2010, 'Total synthesis of (+)- and (-)-galanthamine', Heterocycles, vol. 82, no. 1, pp. 563-597. https://doi.org/10.3987/COM-10-S(E)27
Kato, Tomoaki ; Tanimoto, Hiroki ; Yamada, Hisako ; Chida, Noritaka. / Total synthesis of (+)- and (-)-galanthamine. In: Heterocycles. 2010 ; Vol. 82, No. 1. pp. 563-597.
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