Formal synthesis of (-)-morphine from d-glucal based on the cascade Claisen rearrangement

Hiroki Tanimoto, Ryosuke Saito, Noritaka Chida

研究成果: Article査読

63 被引用数 (Scopus)

抄録

The formal synthesis of (-)-morphine is described. The C-ring in morphine was prepared in an optically pure form from d-glucal using Ferrier's carbocyclization reaction, and the vicinal tertiary and quaternary stereocenters in the C-ring were stereoselectively generated in a one-step reaction based on the cascade sequential Claisen rearrangement of an allylic vicinal diol derivative. After the one-step formation of the dibenzofuran structure, the intramolecular Friedel-Crafts type reaction effectively constructed the ABCE-phenanthrofuran skeleton. Introduction of a tosylamide function, followed by reductive cyclization furnished (-)-dihydroisocodeine, the known synthetic intermediate for (-)-morphine.

本文言語English
ページ(範囲)358-362
ページ数5
ジャーナルTetrahedron Letters
49
2
DOI
出版ステータスPublished - 2008 1 7

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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