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

Hiroki Tanimoto, Tomoaki Kato, Noritaka Chida

研究成果: Article査読

57 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)6267-6270
ページ数4
ジャーナルTetrahedron Letters
48
36
DOI
出版ステータスPublished - 2007 9月 3
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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