First synthesis and utilization of oripavidine - A concise and efficient route to important morphinans and apomorphines

Attila Sipos, Sándor Berényi, S. Antus

Research output: Article

9 Citations (Scopus)

Abstract

The synthesis and transformation of oripavidine (8) offer an efficient and simple route to highly active dopamine agonist apomorphines and a variety of important 14β-hydroxy-morphinan derivatives. Natural origin thebaine (6), the starting compound of the procedure, was converted into its N-{[1,2-bis(ethoxycarbonyl)hydrazinyl]methyl} counterpart. l-Selectride was found to be an efficient agent to perform a one-pot O- and N-deprotection at positions 3 and 17, respectively.

Original languageEnglish
Pages (from-to)1359-1365
Number of pages7
JournalHelvetica Chimica Acta
Volume92
Issue number7
DOIs
Publication statusPublished - júl. 2009

Fingerprint

Morphinans
Thebaine
dopamine
Dopamine Agonists
routes
Derivatives
synthesis
selectride
Dopamine

ASJC Scopus subject areas

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

Cite this

First synthesis and utilization of oripavidine - A concise and efficient route to important morphinans and apomorphines. / Sipos, Attila; Berényi, Sándor; Antus, S.

In: Helvetica Chimica Acta, Vol. 92, No. 7, 07.2009, p. 1359-1365.

Research output: Article

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