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

Tomoaki Kato, Hiroki Tanimoto, Hisako Yamada, Noritaka Chida

研究成果: Article査読

29 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)563-597
ページ数35
ジャーナルHeterocycles
82
1
DOI
出版ステータスPublished - 2010 12月 1

ASJC Scopus subject areas

  • 分析化学
  • 薬理学
  • 有機化学

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