Reactions of nepenthone with chromium(II) reagents in neutral aqueous medium

Károly Micskei, Julianna Gyarmati, Gábor Kovács, Sándor Makleit, Csaba Simon, Zoltán Szabó, János Marton, Sándor Hosztafi, Helmut Reinke, Hans Joachim Drexler

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12 Citations (Scopus)

Abstract

A synthetic method for the selective transformations of a selected morphine alkaloid in neutral aqueous medium is introduced. Full diastereoselectivity was achieved by the transformation of nepenthone (1) with [Cr(ida)(H2O)3] into 2a (20R) showing a complementary method as compared to the reactions with classical reagents to result in 2b (20S). A new unexpected morphine derivative 3 was prepared by a ligand-induced modification of the reaction which involves an unprecedented rearrangement.

Original languageEnglish
Pages (from-to)149-153
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number1
Publication statusPublished - Jan 1 1999

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Keywords

  • 6,14-Ethenomorphinans
  • Chromium(II) complex reagents
  • Morphine alkaloids
  • Organochromium(III) complex intermediates

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Micskei, K., Gyarmati, J., Kovács, G., Makleit, S., Simon, C., Szabó, Z., Marton, J., Hosztafi, S., Reinke, H., & Drexler, H. J. (1999). Reactions of nepenthone with chromium(II) reagents in neutral aqueous medium. European Journal of Organic Chemistry, (1), 149-153.