6-O-demethylation of the thevinols with lithium aluminium hydride: Selective demethylation of a tertiary alkyl methyl ether in the presence of an aryl methyl ether

Simon W. Breeden, Andrew Coop, Stephen M. Husbands, John W. Lewis

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

In the pursuit of ring-constrained analogues of buprenorphine, we wished to prepare 6-O-demethylated analogues of the thevinols and orvinols. Previously it had been disclosed that lithium aluminum hydride (LAH) in THF containing a chlorinated solvent could achieve this transformation. Here we report the results of our work with LAH in the non-coordinating solvent toluene. In refluxing toluene, the selective 6-O-demethylation of thevinols could be achieved with no 3-O-demethylation being observed. It appears that a C(20)-OH or C(20)-NH2 group is needed on the substrate for this hydrogenolysis to proceed.

Original languageEnglish
Pages (from-to)1978-1980
Number of pages3
JournalHelvetica Chimica Acta
Volume82
Issue number11
DOIs
Publication statusPublished - 10 Nov 1999

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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