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

Hiroki Tanimoto, Ryosuke Saito, Noritaka Chida

Research output: Contribution to journalArticle

61 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)358-362
Number of pages5
JournalTetrahedron Letters
Volume49
Issue number2
DOIs
Publication statusPublished - 2008 Jan 7

Keywords

  • Cascade Claisen rearrangement
  • Dihydroisocodeine
  • Friedel-Crafts type cyclization
  • Morphine
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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