Perchloric acid induced epimerisation of the thevinones: An improved synthesis of 7β-dihydrothevinones

Ian Derrick, Andrew Coop, Sali M. Al-Mousawi, Stephen M. Husbands, John W. Lewis

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

The region above and away from C7 in the orvinols is known to be of particular importance in determining the μ-opioid receptor profile of this important class of opioids. However it has been difficult to explore this site due to the relative inaccessibility of 7β-substituted compounds. Here we report that perchloric acid induced epimerisation of the 7α-ketones (dihydrothevinones) allows considerably improved access to a series of β-ketones (β-dihydrothevinones). The extent of epimerisation of the 7α-ketone is determined by the degree of steric bulk in both the 6,14-bridge and in the ketone side chain.

Original languageEnglish
Pages (from-to)7571-7576
Number of pages6
JournalTetrahedron Letters
Volume41
Issue number39
DOIs
Publication statusPublished - 23 Sep 2000

Keywords

  • 7β-dihydrothevinones
  • Epimerisation
  • Opioids
  • Thevinones

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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