Total synthesis of (+)-galanthamine starting from d-glucose

Hiroki Tanimoto, Tomoaki Kato, Noritaka Chida

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Abstract

The stereoselective total synthesis of (+)-galanthamine (+)-1 starting from d-glucose is described. The cyclohexene ring in (+)-1 was prepared in an optically active form from d-glucose using Ferrier's carbocyclization reaction, and the critical quaternary carbon was stereoselectively generated via chirality transfer based on the Claisen rearrangement of a cyclohexenol. The dibenzofuran skeleton was effectively constructed by the bromonium ion-mediated intramolecular cyclization of a cyclohexene possessing a phenolic ether function. After the introduction of a carbon-carbon double bond, the Pictet-Spengler type cyclization, followed by the reduction of the amide function completed the chiral synthesis of (+)-1.

Original languageEnglish
Pages (from-to)6267-6270
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number36
DOIs
Publication statusPublished - 2007 Sep 3

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Keywords

  • Chiral synthesis
  • Claisen rearrangement
  • Galanthamine

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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